Highly Enantioselective Co‐Catalytic Direct Aldol Reactions by Combination of Hydrogen‐Bond Donating and Acyclic Amino Acid Catalysts

Highly enantioselective co-catalytic direct aldol reactions by a combination of simple hydrophobic acyclic amino acid and hydrogen-bond donating catalysts are presented. The corresponding aldol pro ...

[1]  Junliang Sun,et al.  Dynamic one-pot three-component catalytic asymmetric transformation by combination of hydrogen-bond-donating and amine catalysts. , 2011, Angewandte Chemie.

[2]  A. Córdova,et al.  Asymmetric Aza‐Morita–Baylis–Hillman‐Type Reactions: The Highly Enantioselective Reaction between Unmodified α,β‐ Unsaturated Aldehydes and N‐Acylimines by Organo‐co‐catalysis , 2011 .

[3]  Xiangkai Fu,et al.  A Highly Efficient, Large‐Scale, Asymmetric Direct Aldol Reaction Employing Simple Threonine Derivatives as Recoverable Organocatalysts in the Presence of Water , 2011 .

[4]  F. Himo,et al.  Enantioselective Conjugate Silyl Additions to α,β-Unsaturated Aldehydes Catalyzed by Combination of Transition Metal and Chiral Amine Catalysts , 2011 .

[5]  T. Kanemitsu,et al.  L‐t‐Leucine‐Catalyzed Direct Asymmetric Aldol Reaction of Cyclic Ketones , 2011 .

[6]  M. Shoaib,et al.  Practical access to highly enantioenriched quaternary carbon Michael adducts using simple organocatalysts. , 2011, Organic & biomolecular chemistry.

[7]  Junliang Sun,et al.  Dynamic kinetic asymmetric domino oxa-Michael/carbocyclization by combination of transition-metal and amine catalysis: catalytic enantioselective synthesis of dihydrofurans. , 2010, Chemistry.

[8]  A. Chan,et al.  Highly enantioselective and efficient organocatalytic aldol reaction of acetone and β,γ-unsaturated α-keto ester. , 2010, Organic letters.

[9]  Xuebing Ma,et al.  One-step, efficient synthesis of combined threonine–surfactant organocatalysts for the highly enantioselective direct aldol reactions of cyclic ketones with aromatic aldehydes in the presence of water , 2010 .

[10]  J. Neudörfl,et al.  Enantiopure Monoprotected cis‐1,2‐Diaminocyclohexane: One‐Step Preparation and Application in Asymmetric Organocatalysis , 2010 .

[11]  P. Schneider,et al.  Thiazolidine-based organocatalysts for a highly enantioselective direct aldol reaction , 2010 .

[12]  S. Luo,et al.  Chiral primary-tertiary diamine-Brønsted acid salt catalyzed syn-selective cross-aldol reaction of aldehydes. , 2010, The Journal of organic chemistry.

[13]  A. Sakakura,et al.  Organoammonium Salt-Catalyzed Enantioselective Cycloaddition Reactions with α-(Acyloxy)- or α-Diacylaminoacroleins , 2010 .

[14]  F. Ullah,et al.  Dynamic kinetic asymmetric transformation (DYKAT) by combined amine- and transition-metal-catalyzed enantioselective cycloisomerization. , 2010, Chemistry.

[15]  X. Companyó,et al.  Improving Asymmetric Organocatalysts via Supramolecular Interactions , 2010 .

[16]  X. Companyó,et al.  Substrate-dependent nonlinear effects in proline-thiourea-catalyzed aldol reactions: unraveling the role of the thiourea co-catalyst. , 2010, Chemistry.

[17]  G. Upert,et al.  Enamine catalysis with low catalyst loadings--high efficiency via kinetic studies. , 2010, Journal of the American Chemical Society.

[18]  D. Dixon,et al.  Asymmetric organocatalytic relay cascades: catalyst-controlled stereoisomer selection in the synthesis of functionalized cyclohexanes. , 2009, Angewandte Chemie.

[19]  R. Mahrwald,et al.  Asymmetric histidine-catalyzed cross-aldol reactions of enolizable aldehydes: access to defined configured quaternary stereogenic centers. , 2009, Journal of the American Chemical Society.

[20]  P. Pihko Hydrogen bonding in organic synthesis , 2009 .

[21]  T. Rovis,et al.  Asymmetric synthesis of functionalized cyclopentanones via a multicatalytic secondary amine/N-heterocyclic carbene catalyzed cascade sequence. , 2009, Journal of the American Chemical Society.

[22]  K. Jørgensen,et al.  Achieving molecular complexity by organocatalytic one-pot strategies - a fast entry for synthesis of sphingoids, amino sugars, and polyhydroxylated alpha-amino acids. , 2009, Angewandte Chemie.

[23]  L. Crovetto,et al.  Highly enantio- and diastereoselective organocatalytic desymmetrization of prochiral cyclohexanones by simple direct aldol reaction catalyzed by proline. , 2009, Chemistry.

[24]  T. Akiyama,et al.  Enantioselective Robinson-type annulation reaction catalyzed by chiral phosphoric acids. , 2009, Angewandte Chemie.

[25]  Yixin Lu,et al.  Asymmetric catalysis with chiral primary amine-based organocatalysts. , 2009, Chemical communications.

[26]  P. Schreiner,et al.  (Thio)urea organocatalysis--what can be learnt from anion recognition? , 2009, Chemical Society reviews.

[27]  C. Da,et al.  2,4-Dinitrophenol as an effective cocatalyst: greatly improving the activities and enantioselectivities of primary amine organocatalysts for asymmetric aldol reactions. , 2009, The Journal of organic chemistry.

[28]  A. Demir,et al.  Direct enantioselective aldol reactions catalyzed by a proline-thiourea host-guest complex. , 2009, Chemical communications.

[29]  S. Luo,et al.  Chiral primary-tertiary diamine catalysts derived from natural amino acids for syn-aldol reactions of hydroxy ketones. , 2009, The Journal of organic chemistry.

[30]  S. Easwar,et al.  Protonated arginine and lysine as catalysts for the direct asymmetric aldol reaction in ionic liquids , 2008 .

[31]  C. Zhao,et al.  Modularly designed organocatalytic assemblies for direct nitro-Michael addition reactions. , 2008, Angewandte Chemie.

[32]  Tanmay Mandal Dr. and,et al.  Modularly Designed Organocatalytic Assemblies for Direct Nitro-Michael Addition Reactions† , 2008 .

[33]  F. Himo,et al.  Density functional theory study of the stereoselectivity in small peptide-catalyzed intermolecular aldol reactions , 2008 .

[34]  Ying‐Chun Chen The Development of AsymmetricPrimary Amine Catalysts Based on Cinchona Alkaloids , 2008 .

[35]  K. Nakano,et al.  Organocatalytic enantioselective Diels-Alder reaction of dienes with alpha-(N,N-Diacylamino)acroleins. , 2008, Organic letters.

[36]  Yixin Lu,et al.  Primary amino acids: privileged catalysts in enantioselective organocatalysis. , 2008, Organic & biomolecular chemistry.

[37]  J. Fréchet,et al.  One-pot multi-component asymmetric cascade reactions catalyzed by soluble star polymers with highly branched non-interpenetrating catalytic cores. , 2008, Journal of the American Chemical Society.

[38]  Z. Shao,et al.  Advances in asymmetric organocatalytic reactions catalyzed by chiral primary amines , 2008 .

[39]  Changwei Hu,et al.  Asymmetric direct aldol reaction of functionalized ketones catalyzed by amine organocatalysts based on bispidine. , 2008, Journal of the American Chemical Society.

[40]  C. Barbas,et al.  Water-compatible organocatalysts for direct asymmetric syn-aldol reactions of dihydroxyacetone and aldehydes. , 2008, Organic letters.

[41]  Xinhong Yu,et al.  Hydrogen-bond-mediated asymmetric catalysis. , 2008, Chemistry, an Asian journal.

[42]  A. Córdova,et al.  A kinetic and mechanistic study of the amino acid catalyzed aldol condensation of acetaldehyde in aqueous and salt solutions. , 2008, The journal of physical chemistry. A.

[43]  Steven M. Mennen,et al.  Asymmetric catalysis mediated by synthetic peptides. , 2007, Chemical reviews.

[44]  K. Pluhackova,et al.  Vicinal amino alcohols as organocatalysts in asymmetric cross-aldol reaction of ketones: application in the synthesis of convolutamydine A. , 2007, Organic letters.

[45]  L. Gong,et al.  Design of organocatalysts for asymmetric direct syn-aldol reactions. , 2007, Organic letters.

[46]  A. Córdova,et al.  Aza-Morita–Baylis–Hillman-type reactions: highly enantioselective organocatalytic addition of unmodified α,β-unsaturated aldehydes to N-Boc protected imines , 2007 .

[47]  A. Córdova,et al.  A one-pot combination of amine and heterocyclic carbene catalysis: direct asymmetric synthesis of β-hydroxy and β-malonate esters from α,β-unsaturated aldehydes , 2007 .

[48]  F. Tanaka,et al.  Mimicking aldolases through organocatalysis: syn-selective aldol reactions with protected dihydroxyacetone. , 2007, Organic letters.

[49]  F. Tanaka,et al.  Mimicking fructose and rhamnulose aldolases: organocatalytic syn-aldol reactions with unprotected dihydroxyacetone. , 2007, Angewandte Chemie.

[50]  K. Nakano,et al.  Enantioselective [2+2] cycloaddition of unactivated alkenes with alpha-acyloxyacroleins catalyzed by chiral organoammonium salts. , 2007, Journal of the American Chemical Society.

[51]  Yong‐Chua Teo,et al.  Direct asymmetric aldol reactions catalyzed by a siloxy serine organocatalyst in water , 2007 .

[52]  Han-Ming Shen,et al.  Highly Efficient Threonine-Derived Organocatalysts for Direct Asymmetric Aldol Reactions in Water , 2007 .

[53]  Yixin Lu,et al.  Direct asymmetric three-component organocatalytic anti-selective Mannich reactions in a purely aqueous system. , 2007, Organic & biomolecular chemistry.

[54]  A. Córdova,et al.  Enantioselective organocatalytic conjugate addition of amines to α,β-unsaturated aldehydes: one-pot asymmetric synthesis of β-amino acids and 1,3-diamines , 2007 .

[55]  Long Zhang,et al.  A simple primary-tertiary diamine-Brønsted acid catalyst for asymmetric direct aldol reactions of linear aliphatic ketones. , 2007, Journal of the American Chemical Society.

[56]  T. Kano,et al.  syn-selective and enantioselective direct cross-aldol reactions between aldehydes catalyzed by an axially chiral amino sulfonamide. , 2007, Angewandte Chemie.

[57]  F. Tanaka,et al.  Direct catalytic asymmetric synthesis of anti-1,2-amino alcohols and syn-1,2-diols through organocatalytic anti-Mannich and syn-aldol reactions. , 2007, Journal of the American Chemical Society.

[58]  D. Deng,et al.  Stereoselective aldol reactions catalyzed by acyclic amino acids in aqueous micelles , 2007 .

[59]  J. Háfren,et al.  The small peptide-catalyzed direct asymmetric aldol reaction in water. , 2006, Organic & biomolecular chemistry.

[60]  Bernd Schetter,et al.  Aldolreaktionen in der Totalsynthese von Polyketiden , 2006 .

[61]  R. Mahrwald,et al.  Modern aldol methods for the total synthesis of polyketides. , 2006, Angewandte Chemie.

[62]  Yan Zhou,et al.  Chiral diols: a new class of additives for direct aldol reaction catalyzed by L-proline. , 2006, The Journal of organic chemistry.

[63]  A. Sakakura,et al.  Enantioselective Diels–Alder Reaction of α‐Acyloxyacroleins Catalyzed by Chiral 1,1′‐Binaphthyl‐2,2′‐diammonium Salts , 2006 .

[64]  Shaowu Wang,et al.  Highly efficient and reusable dendritic catalysts derived from N-prolylsulfonamide for the asymmetric direct aldol reaction in water. , 2006, Organic letters.

[65]  A. Córdova,et al.  Direct asymmetric intermolecular aldol reactions catalyzed by amino acids and small peptides. , 2006, Chemistry.

[66]  Yixin Lu,et al.  Asymmetric aldol reactions catalyzed by tryptophan in water. , 2006, Chemical communications.

[67]  K. Nakano,et al.  Chiral 1,1'-binaphthyl-2,2'-diammonium salt catalysts for the enantioselective Diels-Alder reaction with alpha-acyloxyacroleins. , 2006, Organic letters.

[68]  A. Córdova,et al.  Direct catalytic intermolecular alpha-allylic alkylation of aldehydes by combination of transition-metal and organocatalysis. , 2006, Angewandte Chemie.

[69]  A. Córdova,et al.  Small peptide-catalyzed enantioselective addition of ketones to nitroolefins , 2006 .

[70]  A. Córdova,et al.  Simple highly modular acyclic amine-catalyzed direct enantioselective addition of ketones to nitro-olefins. , 2006, Chemical communications.

[71]  A. Córdova,et al.  Acyclic chiral amines and amino acids as inexpensive and readily tunable catalysts for the direct asymmetric three-component Mannich reaction. , 2005, Chemistry.

[72]  F. Himo,et al.  The origin of stereoselectivity in primary amino acid catalyzed intermolecular aldol reactions. , 2005, Angewandte Chemie.

[73]  Yong Huang,et al.  Enantioselective organo-cascade catalysis. , 2005, Journal of the American Chemical Society.

[74]  A. Córdova,et al.  Small peptides as modular catalysts for the direct asymmetric aldol reaction: ancient peptides with aldolase enzyme activity. , 2005, Chemical communications.

[75]  S. Gellman,et al.  Diphenylprolinol methyl ether: a highly enantioselective catalyst for Michael addition of aldehydes to simple enones. , 2005, Organic letters.

[76]  A. Córdova,et al.  Amino acid catalyzed neogenesis of carbohydrates: a plausible ancient transformation. , 2005, Chemistry.

[77]  J. E. Thomson,et al.  Highly enantioselective organocatalysis of the Hajos-Parrish-Eder-Sauer-Wiechert reaction by the beta-amino acid cispentacin. , 2005, Chemical communications.

[78]  S. Gellman,et al.  Enantioselective organocatalytic Michael additions of aldehydes to enones with imidazolidinones: cocatalyst effects and evidence for an enamine intermediate. , 2005, Journal of the American Chemical Society.

[79]  A. Córdova,et al.  Acyclic amino acid-catalyzed direct asymmetric aldol reactions: alanine, the simplest stereoselective organocatalyst. , 2005, Chemical communications.

[80]  K. Nakano,et al.  Design of an organocatalyst for the enantioselective Diels-Alder reaction with alpha-acyloxyacroleins. , 2005, Journal of the American Chemical Society.

[81]  B. Westermann,et al.  Dihydroxyaceton in Aminosäure-katalysierten Mannich-Reaktionen† , 2005 .

[82]  B. Westermann,et al.  Dihydroxyacetone in amino acid catalyzed Mannich-type reactions. , 2005, Angewandte Chemie.

[83]  S. Tsogoeva,et al.  (S)-Histidine-based dipeptides as organic catalysts for direct asymmetric aldol reactions , 2005 .

[84]  D. Enders,et al.  Die Dihydroxyaceton‐Einheit – ein nützlicher C3‐Baustein in der Organischen Synthese , 2005 .

[85]  D. Enders,et al.  The dihydroxyacetone unit--a versatile C(3) building block in organic synthesis. , 2005, Angewandte Chemie.

[86]  D. Enders,et al.  Direkte organokatalytische De‐novo‐Synthese von Kohlenhydraten , 2005 .

[87]  D. Enders,et al.  Direct organocatalytic de novo synthesis of carbohydrates. , 2005, Angewandte Chemie.

[88]  A. Córdova,et al.  Direct Amino Acid Catalyzed Asymmetric α Oxidation of Ketones with Molecular Oxygen , 2004 .

[89]  T. Mukaiyama Strategien zur Erforschung neuer Reaktionen , 2004 .

[90]  T. Mukaiyama Explorations into new reaction chemistry. , 2004, Angewandte Chemie.

[91]  Peter I. Dalko,et al.  Im Goldenen Zeitalter der Organokatalyse , 2004 .

[92]  P. Dalko,et al.  In the golden age of organocatalysis. , 2004, Angewandte Chemie.

[93]  Claudio Palomo,et al.  Current progress in the asymmetric aldol addition reaction. , 2004, Chemical Society reviews.

[94]  Yong Huang,et al.  Hydrogen bonding: Single enantiomers from a chiral-alcohol catalyst , 2003, Nature.

[95]  Davidr . Evans,et al.  Ni(II) bis(oxazoline)-catalyzed enantioselective syn aldol reactions of N-propionylthiazolidinethiones in the presence of silyl triflates. , 2003, Journal of the American Chemical Society.

[96]  S. Matsunaga,et al.  Direct catalytic asymmetric Michael reaction of hydroxyketones: asymmetric Zn catalysis with a Et2Zn/linked-BINOL complex. , 2003, Journal of the American Chemical Society.

[97]  P. Váchal,et al.  Structure-based analysis and optimization of a highly enantioselective catalyst for the strecker reaction. , 2002, Journal of the American Chemical Society.

[98]  B. List Proline-catalyzed asymmetric reactions , 2002 .

[99]  P. Schreiner,et al.  H-bonding additives act like Lewis acid catalysts. , 2002, Organic letters.

[100]  C. Barbas,et al.  Amino acid catalyzed direct asymmetric aldol reactions: a bioorganic approach to catalytic asymmetric carbon-carbon bond-forming reactions. , 2001, Journal of the American Chemical Society.

[101]  B. Trost,et al.  Asymmetric Aldol Reaction via a Dinuclear Zinc Catalyst: α-Hydroxyketones as Donors , 2001 .

[102]  R. Sheldon,et al.  A four-step enzymatic cascade for the one-pot synthesis of non-natural carbohydrates from glycerol. , 2000, The Journal of organic chemistry.

[103]  Davidr . Evans,et al.  Application of Complex Aldol Reactions to the Total Synthesis of Phorboxazole B , 2000 .

[104]  S. Denmark,et al.  The Chemistry of Trichlorosilyl Enolates. Aldol Addition Reactions of Methyl Ketones , 2000 .

[105]  B. List,et al.  Catalytic Asymmetric Synthesis of anti-1,2-Diols , 2000 .

[106]  Shuj Kobayashi,et al.  Highly anti-Selective Catalytic Asymmetric Aldol Reactions , 2000 .

[107]  Chi-Huey Wong,et al.  Die katalysierte asymmetrische Aldolreaktion , 2000 .

[108]  Wong,et al.  The Catalytic Asymmetric Aldol Reaction. , 2000, Angewandte Chemie.

[109]  J. S. Johnson,et al.  Chiral bis(oxazoline) copper(II) complexes: versatile catalysts for enantioselective cycloaddition, Aldol, Michael, and carbonyl ene reactions. , 2000, Accounts of chemical research.

[110]  K. Nicolaou,et al.  Der Stand der Totalsynthese zu Beginn des 21. Jahrhunderts , 2000 .

[111]  Baran,et al.  The Art and Science of Total Synthesis at the Dawn of the Twenty-First Century. , 2000, Angewandte Chemie.

[112]  K. Jørgensen,et al.  Catalytic asymmetric homo-aldol reaction of pyruvate—a chiral Lewis acid catalyst that mimics aldolase enzymes , 2000 .

[113]  C. Barbas,et al.  Enantioselective aldol cyclodehydrations catalyzed by antibody 38C2. , 1999, Organic letters.

[114]  Yoichi M. A. Yamada,et al.  Direct Catalytic Asymmetric Aldol Reaction , 1999 .

[115]  Yoichi M. A. Yamada,et al.  Direct Catalytic Asymmetric Aldol Reactions of Aldehydes with Unmodified Ketones , 1997 .

[116]  Masakatsu Shibasaki,et al.  Direkte katalytische asymmetrische Aldolreaktionen von Aldehyden mit nicht modifizierten Ketonen , 1997 .

[117]  Richard A. Lerner,et al.  Antibody-Catalyzed Enantioselective Robinson Annulation , 1997 .

[118]  Chi-Huey Wong,et al.  Recent Advances in the Chemoenzymatic Synthesis of Carbohydrates and Carbohydrate Mimetics. , 1996, Chemical reviews.

[119]  G. E. Keck,et al.  Catalytic Enantioselective Synthesis of Dihydropyrones via Formal Hetero Diels-Alder Reactions of "Danishefsky's Diene" with Aldehydes , 1995 .

[120]  K. Mikami,et al.  Asymmetric Catalytic Aldol-type Reaction with Ketene Silyl Acetals: Possible Intervention of the Silatropic Ene Pathway , 1994 .

[121]  Jean-Marie Lehn,et al.  Perspectives in Supramolecular Chemistry—From Molecular Recognition towards Molecular Information Processing and Self‐Organization , 1990 .

[122]  J. Lehn,et al.  Perspektiven der Supramolekularen Chemie – von der molekularen Erkennung zur molekularen Informationsverarbeitung und Selbstorganisation , 1990 .

[123]  E. Corey,et al.  Enantioselective total synthesis of a protosterol, 3.beta.,20-dihydroxyprotost-24-ene , 1990 .

[124]  S. Danishefsky,et al.  THE PYRIDINE ROUTE TO OPTICALLY ACTIVE ESTRONE AND 19-NORSTEROIDS , 1975 .

[125]  S. Danishefsky,et al.  Letter: The pyridine route to optically active estrone and 19-norsteroids. , 1975, Journal of the American Chemical Society.

[126]  D. R. Parrish,et al.  Asymmetric synthesis of bicyclic intermediates of natural product chemistry , 1974 .

[127]  R. Wiechert,et al.  Neuartige asymmetrische Cyclisierung zu optisch aktiven Steroid‐CD‐Teilstücken , 1971 .