Reversal of diastereoselectivity in the benzylation of the lithium enolates of phosphonopropanoamides by changing the base equivalents

[1]  Delong Liu,et al.  Reversal in enantioselectivity for the palladium-catalyzed asymmetric allylic substitution with novel metallocene-based planar chiral diphosphine ligands , 2008 .

[2]  S. Luis,et al.  Efficient chirality switching in the addition of diethylzinc to aldehydes in the presence of simple chiral alpha-amino amides. , 2007, Angewandte Chemie.

[3]  O. García-Barradas,et al.  A Convenient Method for the Preparation of Chiral Phosphonoacetamides and Their Horner—Wadsworth—Emmons Reaction. , 2007 .

[4]  Antonio Ramirez,et al.  Lithium diisopropylamide: solution kinetics and implications for organic synthesis. , 2007, Angewandte Chemie.

[5]  P. Stephens,et al.  Asymmetric Michael reaction: novel efficient access to chiral β-ketophosphonates , 2007 .

[6]  W. Zeng,et al.  Hydrogen-bonding directed reversal of enantioselectivity. , 2007, Journal of the American Chemical Society.

[7]  J. Lex,et al.  Reversal of Enantioselectivity by Catalyst Protonation: Asymmetric ­Hydrocyanation of Imines with Oxazaborolidines , 2006 .

[8]  J. D'angelo,et al.  The asymmetric Michael-type alkylation of chiral β-enamino esters: critical role of a benzyl ester group in the racemization of adducts , 2005 .

[9]  J. Vicario,et al.  (S,S)-(+)-pseudoephedrine as chiral auxiliary in asymmetric aza-Michael reactions. Unexpected selectivity change when manipulating the structure of the auxiliary. , 2005, The Journal of organic chemistry.

[10]  T. Igarashi,et al.  Small amounts of achiral beta-amino alcohols reverse the enantioselectivity of chiral catalysts in cooperative asymmetric autocatalysis. , 2005, Journal of the American Chemical Society.

[11]  D. Du,et al.  Asymmetric Henry reaction catalyzed by C2-symmetric tridentate bis(oxazoline) and bis(thiazoline) complexes: metal-controlled reversal of enantioselectivity. , 2005, The Journal of organic chemistry.

[12]  C. Cativiela,et al.  Asymmetric alkylation of dimethoxyphosphoryl-N-[1-(S)-alpha-methylbenzyl]acetamide enolates. Synthesis of both stereoisomers from the same source of chirality by changing the equivalents of LDA. , 2005, Chemical communications.

[13]  L. Belvisi,et al.  Stereoselective synthesis of Cα-tetrasubstituted azabicyclo[X.3.0]alkane amino acids , 2004 .

[14]  A. Wagner,et al.  Kinetic resolution of amines: a highly enantioselective and chemoselective acetylating agent with a unique solvent-induced reversal of stereoselectivity. , 2004, Angewandte Chemie.

[15]  C. Casey,et al.  Reversal of enantioselectivity in the hydroformylation of styrene with [2S,4S-BDPP]Pt(SnCl3)Cl at high temperature arises from a change in the enantioselective-determining step. , 2004, Journal of the American Chemical Society.

[16]  M. Huffman,et al.  Michael reactions of pseudoephedrine amide enolates: effect of LiCl on syn/anti selectivity. , 2004, The Journal of organic chemistry.

[17]  B. Trost,et al.  Direct catalytic asymmetric aldol additions of methyl ynones. Spontaneous reversal in the sense of enantioinduction. , 2004, Journal of the American Chemical Society.

[18]  S. Tomoda,et al.  Origin of stereochemical reversal in Meyers-type enolate alkylations. Importance of intramolecular Li coordination and solvent effects. , 2004, Organic letters.

[19]  Jian Zhou,et al.  Controllable enantioselective Friedel-Crafts reaction between indoles and alkylidene malonates catalyzed by pseudo-C3-symmetric trisoxazoline copperII complexes. , 2004, The Journal of organic chemistry.

[20]  H. Danjo,et al.  P-stereogenic P/N hybrid ligands: a remarkable switch in enantioselectivity in palladium-catalyzed asymmetric allylation ☆ , 2004 .

[21]  M. Bergdahl,et al.  The remarkable ability of lithium ion to reverse the stereoselectivity in the conjugate addition of Li[BuCuI] to a chiral N-crotonyl-2-oxazolidinone. , 2003, Organic letters.

[22]  S. Tomoda,et al.  Origin of stereochemistry in Meyers enolate alkylations. Importance of major enolate structure and population in tetrahydrofuran , 2003 .

[23]  M. Franzini,et al.  Toggling enantioselective catalysis--a promising paradigm in the development of more efficient and versatile enantioselective synthetic methodologies. , 2003, Chemical Society reviews.

[24]  K. Furusawa,et al.  Efficient stereodivergent synthesis of erythro- and threo-sphingosines: unprecedented reversal of the stereochemistry in the addition , 2002 .

[25]  M. Sibi,et al.  Temperature dependent reversal of stereochemistry in enantioselective conjugate amine additions , 2002 .

[26]  B. Feringa,et al.  Copper phosphoramidite catalyzed enantioselective ring-opening of oxabicyclic alkenes: remarkable reversal of stereocontrol. , 2002, Organic letters.

[27]  R. K. Boeckman,et al.  Toward the development of a general chiral auxiliary. 9. Highly diastereoselective alkylations and acylations to form tertiary and quaternary centers. , 2001, Organic letters.

[28]  M. Kanai,et al.  Switching enantiofacial selectivities using one chiral source: catalytic enantioselective synthesis of the key intermediate for (20S)-camptothecin family by (S)-selective cyanosilylation of ketones. , 2001, Journal of the American Chemical Society.

[29]  M. Sibi,et al.  Reversal of Stereochemistry in Enantioselective Transformations. Can They Be Planned or Are They Just Accidental , 2001 .

[30]  A. Meyers,et al.  Chiral Non-Racemic Bicyclic Lactams. Auxiliary-Based Asymmetric Reactions , 2000 .

[31]  Yoshihiko Ito,et al.  Catalytic asymmetric hydrogenation of α-(acetamido)acrylates using TRAP trans-chelating chiral bisphosphine ligands: Remarkable effects of ligand P-substituent and hydrogen pressure on enantioselectivity , 2000 .

[32]  E. Juaristi,et al.  Stereoselective alkylation of C2-symmetric chiral N-phthaloylglycinamides in the preparation of enantiopure α-amino acids , 2000 .

[33]  N. Nomura,et al.  Substituent Effects of Ligands on Asymmetric Induction in a Prototypical Palladium-Catalyzed Allylation Reaction: Making Both Enantiomers of a Product in High Optical Purity Using the Same Source of Chirality , 1999 .

[34]  M. Murakami,et al.  CATALYTIC ASYMMETRIC 4 + 1 CYCLOADDITION OF VINYLALLENES WITH CARBON MONOXIDE : REVERSAL OF THE INDUCED CHIRALITY BY THE CHOICE OF METAL , 1999 .

[35]  S. Kobayashi,et al.  A switch of enantiofacial selectivity in chiral ytterbium-catalyzed 1,3-dipolar cycloaddition reactions , 1999 .

[36]  J. Blake,et al.  Stereoselective Alkylations in Rigid Systems. Effect of Remote Substituents on π-Facial Additions to Lactam Enolates. Stereoelectronic and Steric Effects , 1998 .

[37]  K. Gothelf,et al.  MOLECULAR SIEVE DEPENDENT ABSOLUTE STEREOSELECTIVITY IN ASYMMETRIC CATALYTIC 1,3-DIPOLAR CYCLOADDITION REACTIONS , 1998 .

[38]  N. Nomura,et al.  Unprecedented Electronic and Steric Effects in Palladium-Catalyzed Asymmetric Allylation: Switching of Enantioselectivity with a Single Chiral Backbone , 1996 .

[39]  A. Myers,et al.  Practical Syntheses of Enantiomerically Enriched γ-Lactones and γ-Hydroxy Ketones by the Alkylation of Pseudoephedrine Amides with Epoxides and Their Derivatives , 1996 .

[40]  C. Alvarez-Ibarra,et al.  Asymmetric Alkylation of 8-Phenylmenthyl N-[Bis(methylthio)methylene]glycinate Enolates. Synthesis of D- and L-.alpha.-Amino Acids from a Single Chiral Precursor , 1995 .

[41]  K. Ohe,et al.  Chiral Oxazolinylferrocene-Phosphine Hybrid Ligand for the Asymmetric Hydrosilylation of Ketones , 1995 .

[42]  J. L. Gleason,et al.  Practical method for the synthesis of D- or L-.alpha.-amino acids by the alkylation of (+)- or (-)-pseudoephedrine glycinamide. , 1995 .

[43]  J. D'angelo,et al.  Methyl methacrylate as acceptor in the asymmetric Michael reaction using chiral β-enaminoesters: Simultaneous, complete stereocontrol of a quaternary carbon center and a tertiary one in the β-position , 1995 .

[44]  T. Kawabata,et al.  Direct Asymmetric .alpha.-Alkylation of Phenylalanine Derivatives Using No External Chiral Sources , 1994 .

[45]  J. L. Gleason,et al.  Use of Pseudoephedrine as a Practical Chiral Auxiliary for Asymmetric Synthesis , 1994 .

[46]  H. Ishitani,et al.  Lanthanide (III)-catalyzed enantioselective Diels-Alder reactions. Stereoselective synthesis of both enantiomers by using a single chiral source and a choice of achiral ligands , 1994 .

[47]  R. Bridges,et al.  2,3-Pyrrolidinedicarboxylates as Neurotransmitter Conformer Mimics: Enantioselective Synthesis via Chelation-Controlled Enolate Alkylation , 1994 .

[48]  I. Hachiya,et al.  Asymmetric Diels-Alder reactions catalyzed by chiral lanthanide(III) trifluoromethanesulfonates. Unique structure of the triflate and stereoselective synthesis of both enantiomers using a single chiral source and a choice of achiral ligands , 1994 .

[49]  K. Tomioka,et al.  Solvent effect and NMR behaviour in a chiral amidophosphine mediated reaction of organocuprate with chalcone , 1993 .

[50]  D. Romo,et al.  Chiral non-racemic bicyclic lactams. Vehicles for the construction of natural and unnatural products containing quaternary carbon centers. , 1991 .

[51]  Robert M. Williams,et al.  Asymmetric synthesis of monosubstituted and .alpha.,.alpha.-disubstituted .alpha.-amino acids via diastereoselective glycine enolate alkylations , 1991 .

[52]  D. Seebach,et al.  Herstellung chiraler elektrophiler Glycin- und (E)-2,3-Dehydroaminosäure-Derivate aus 2-t-Butyl-3-methyl-4-oxo-1-imidazolidincarbonsäure-t-butylester (Boc-BMI) , 1991 .

[53]  P. Wipf,et al.  Stereochemical control in the ester enolate Claisen rearrangement. 2. Chairlike vs boatlike transition-state selection , 1991 .

[54]  S. Kiyooka,et al.  Dramatic changes in diastereoselectivity with the quantity of titanium tetrachloride used in Lewis acid mediated reactions of allylsilane with .alpha.-amino aldehydes , 1989 .

[55]  D. Seebach Structure and Reactivity of Lithium Enolates. From Pinacolone to Selective C‐Alkylations of Peptides. Difficulties and Opportunities Afforded by Complex Structures , 1988 .

[56]  J. McCauley,et al.  Opposite high diastereoselectivity in the carbonyl addition of organolithium and Grignard reagents to 3-acylisoxazolines , 1985 .

[57]  K. Tomioka,et al.  Asymmetric alkylation of .alpha.-alkyl .beta.-keto esters , 1984 .

[58]  G. Thyagarajan,et al.  Michaelis-Arbuzov rearrangement , 1981 .