Novel and Efficient Approach to Fluorinated β‐Aminobutanones Catalyzed by Molecular Iodine

Abstract A variety of fluorinated compounds of β‐amino ketones could be obtained in good to excellent yields at room temperature through a three‐component Mannich reaction of aldehydes, anilines, and acetones catalyzed by iodine.

[1]  Yanguang Wang,et al.  Molecular iodine-catalyzed one-pot synthesis of substituted quinolines from imines and aldehydes , 2006 .

[2]  Ju Tsung Liu,et al.  Iodine catalyzed conjugate addition of mercaptans to α,β- unsaturated carboxylic acids under solvent-free condition , 2006 .

[3]  B. Das,et al.  Convenient and facile cross-Aldol condensation catalyzed by molecular iodine: An efficient synthesis of α,α′-bis(substituted-benzylidene) cycloalkanones , 2006 .

[4]  H. Kunz,et al.  Kohlenhydrate als chirale Matrices: Stereoselektive Tandem-Mannich-Michael-Reaktionen zur Synthese von Piperidin-Alkaloiden†‡ , 2006 .

[5]  T. Arai,et al.  Mannich-Type Reaction Using Alkenyl Trichloroacetates Catalyzed by Dibutyltin Dimethoxide , 2005 .

[6]  M. Xia,et al.  Molecular iodine-catalyzed imino-diels-alder reactions : Efficient one-pot synthesis of pyrano[3,2-c]quinolines , 2005 .

[7]  C. Yao,et al.  Molecular iodine-catalyzed one-pot synthesis of 4-substituted-1,4-dihydropyridine derivatives via Hantzsch reaction , 2005 .

[8]  M. Snapper,et al.  Practical and highly enantioselective synthesis of beta-alkynyl-beta-amino esters through Ag-catalyzed asymmetric mannich reactions of silylketene acetals and alkynyl imines. , 2005, Organic letters.

[9]  Wei‐Yi Chen,et al.  Molecular-Iodine-Catalyzed One-Pot Synthesis of 1,5-Benzodiazepine Derivatives under Solvent-Free Conditions , 2005 .

[10]  H. Tian,et al.  Rare earth perfluorooctanoate [RE(PFO)3] catalyzed one-pot Mannich reaction: three component synthesis of β-amino carbonyl compounds , 2005 .

[11]  Thierry Ollevier,et al.  Bismuth Triflate-Catalyzed Three-Component Mannich-Type Reaction , 2004 .

[12]  N. Miyoshi,et al.  Solvent-free Imino-Aldol Three-component Couplings on a Conveniently-prepared and Reusable Phosphoric Acid-Silica Gel Support , 2004 .

[13]  B. Han,et al.  Mannich reaction using acidic ionic liquids as catalysts and solvents , 2004 .

[14]  A. Córdova.  The direct catalytic asymmetric mannich reaction. , 2004, Accounts of chemical research.

[15]  B. Karimi,et al.  N-Bromosuccinimideand Iodine Catalyzed Highly Efficient Deoxygenation ofSulfoxides to Thioethers Using 3-Mercaptopropionic Acid under Mild ReactionConditions , 2003 .

[16]  Shuj Kobayashi,et al.  Mannich-type reactions in water using a hydrophobic polymer-supported sulfonic acid catalyst , 2003 .

[17]  K N Houk,et al.  Origins of opposite absolute stereoselectivities in proline-catalyzed direct Mannich and aldol reactions. , 2003, Organic letters.

[18]  R. Matsubara,et al.  Catalytic, asymmetric Mannich-type reactions of N-acylimino esters: reactivity, diastereo- and enantioselectivity, and application to synthesis of N-acylated amino acid derivatives. , 2003, Journal of the American Chemical Society.

[19]  G. Celentano,et al.  Poly(Ethylene Glycol)‐Supported Proline: A Versatile Catalyst for the Enantioselective Aldol and Iminoaldol Reactions , 2002 .

[20]  J. Takaya,et al.  Brønsted Acid‐Catalyzed Mannich‐Type Reactions in Aqueous Media , 2002 .

[21]  B. Ranu,et al.  Zinc tetrafluoroborate catalyzed Mannich-type reaction of aldimines and silyl enol ethers in aqueous medium , 2002 .

[22]  J. Park,et al.  Ytterbium(III) Triflate-Catalyzed One-Pot Mannich-Type Reaction in Ionic Liquid , 2002 .

[23]  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.

[24]  C. Barbas,et al.  Amine-catalyzed direct asymmetric Mannich-type reactions , 2001 .

[25]  D. Russowsky,et al.  Addition of silylated carbon nucleophiles to iminium and cyclic N-acyliminium ions promoted by InCl3 , 2000 .

[26]  T. Loh,et al.  Three Component Synthesis of β-Amino Carbonyl Compounds Using Indium Trichloride-Catalyzed One-pot Mannich-type Reaction in Water , 2000 .

[27]  Shuj Kobayashi,et al.  Mannich-Type Reactions of Aldehydes, Amines, and Ketones in a Colloidal Dispersion System Created by a Brønsted Acid−Surfactant-Combined Catalyst in Water , 1999 .

[28]  J. Takaya,et al.  Chemoselective Activation of Aldimine in Preference to Aldehyde by the Combination of BF3•OEt2 and Water: Novel Catalyst for the Mannich-type Reaction , 1999 .

[29]  S. Nagayama,et al.  Ln(OTf)3- or Cu(OTf)2-Catalyzed Mannich-Type Reactions of Aldhehydes, Amines and Silyl Enolates in Micellar Systems. Facile Synthesis of β-Amino Ketones and Esters in Water , 1999 .

[30]  Yinglin Han,et al.  Gallium enolate-mediated intermolecular aldol reaction and addition reaction of α-bromoketone with imine , 1998 .

[31]  Michael Arend,et al.  Modern Variants of the Mannich Reaction. , 1998, Angewandte Chemie.

[32]  T. Loh,et al.  Novel one-pot Mannich-type reaction in water: Indium trichloride-catalyzed condensation of aldehydes, amines and silyl enol ethers for the synthesis of β-amino ketones and esters , 1998 .

[33]  S. Nagayama,et al.  Aldehydes vs Aldimines. Unprecedented Aldimine-Selective Nucleophilic Additions in the Coexistence of Aldehydes Using a Lanthanide Salt as a Lewis Acid Catalyst , 1997 .

[34]  S. Nagayama,et al.  Aldehydes vs Aldimines. Unprecedented Reactivity in Their Enolate Addition Reactions. , 1997, The Journal of organic chemistry.

[35]  D. Enders,et al.  Efficient Regio‐ and Enantioselective Mannich Reactions , 1996 .

[36]  A. Katritzky,et al.  A Novel and Convenient Preparation of 1-(γ-Aminoalkyl)-Substituted 1,2,4-Triazoles , 1996 .

[37]  Mitsuharu Araki,et al.  One-pot synthesis of β-amino esters from aldehydes using lanthanide triflate as a catalyst , 1995 .

[38]  H. Ishitani,et al.  A novel Mannich-type reaction in aqueous media. Lanthanide triflate-catalysed condensation of aldehydes, amines and vinyl ethers for the synthesis of β-amino ketones , 1995 .

[39]  C. Wermuth,et al.  TMSO-triflate-assisted addition of enols to heteroaromatic imines or hydroxyaminal intermediates , 1994 .

[40]  A. Katritzky,et al.  Additions of 1-(.alpha.-aminoalkyl)benzotriazoles to enol ethers. New routes to 1,3-amino ethers , 1992 .

[41]  E. G. Nolen,et al.  DIASTEREOSELECTIVITY IN THE SYNTHESIS OF MANNICH BASES , 1991 .

[42]  B. Trost,et al.  Comprehensive organic synthesis : selectivity, strategy & efficiency in modern organic chemistry , 1991 .

[43]  E. Kleinman.  The Bimolecular Aliphatic Mannich and Related Reactions , 1991 .

[44]  H. Mosher,et al.  exo,endo-3-[(Dimethylamino)methyl]-d-camphor: d-camphor Mannich products , 1988 .

[45]  J. Roberts,et al.  A new regiospecific synthesis of enol boranes of methyl ketones , 1987 .

[46]  N. Holy,et al.  The mannich reaction-II : Derivatization of aldehydes and ketones using dimethyl(methylene)ammonium salts , 1979 .

[47]  J. E. Dolfini,et al.  Chlorination of the cephem dihydrothiazine ring. Factors influencing C-2 substitution vs. degradation to isothiazoles1 , 1978 .