Asymmetric benzoin reaction catalyzed by benzoylformate decarboxylase

Abstract Aromatic aldehydes are converted into benzoins by benzoylformate decarboxylase catalyzed C–C bond formation. The reaction affords ( R )-benzoins with high enantiomeric excess and in good chemical yields. A broad range of aromatic aldehydes can be used as substrates in aqueous buffer or buffer/DMSO-solutions.

[1]  Stephen Hanessian,et al.  Total synthesis of natural products, the "Chiron" approach , 1983 .

[2]  H. Stetter,et al.  Über die präparative Nutzung der Thiazoliumsalz-katalysierten Acyloin- und Benzoin-Bildung, I. Herstellung von einfachen Acyloinen und Benzoinen , 1976 .

[3]  G. Petsko,et al.  The crystal structure of benzoylformate decarboxylase at 1.6 A resolution: diversity of catalytic residues in thiamin diphosphate-dependent enzymes. , 1998, Biochemistry.

[4]  Kaoru Nakamura,et al.  Enantio- and regioselective reduction of α-diketones by baker's yeast , 1996 .

[5]  K. Sharpless,et al.  .alpha.-Hydroxy ketones in high enantiomeric purity from asymmetric dihydroxylation of enol ethers , 1992 .

[6]  D. Gala,et al.  Preparations of antifungal Sch 42427/SM 9164: Preparative chromatographic resolution, and total asymmetric synthesis via enzymatic preparation of chiral α-hydroxy arylketones , 1996 .

[7]  W. Adam,et al.  Kinetic resolution of chiral α-hydroperoxy esters by horseradish peroxidase-catalyzed enantioselective reduction to α-hydroxy esters , 1995 .

[8]  W. Adam,et al.  Enantioselective oxidation of vic-diols to optically active α-hydroxy ketones by a fructose-derived dioxirane , 1998 .

[9]  A. G. Perkin LXI.—Action of nitric acid on anthracene , 1891 .

[10]  S. Inoue,et al.  Selective cross-acyloin condensation catalyzed by thiazolium salt. Formation of 1-hydroxy 2-one from formaldehyde and other aldehydes , 1985 .

[11]  P. Babbitt,et al.  Mandelate pathway of Pseudomonas putida: sequence relationships involving mandelate racemase, (S)-mandelate dehydrogenase, and benzoylformate decarboxylase and expression of benzoylformate decarboxylase in Escherichia coli. , 1990, Biochemistry.

[12]  G. Hegeman [89] Benzoylformate decarboxylase (Pseudomonas putida)☆ , 1970 .

[13]  G. Coppola,et al.  α-hydroxy acids in enantioselective syntheses , 1997 .

[14]  P. Siegert,et al.  Application of α-keto acid decarboxylases in biotransformations , 1998 .

[15]  W. Adam,et al.  Dimethyldioxirane Oxidation of Titanium Enolates: Diastereoselective .alpha.-Hydroxylations , 1994 .

[16]  R. Csuk,et al.  Baker's yeast mediated transformations in organic chemistry , 1991 .

[17]  W. Adam,et al.  Synthesis of optically active α-hydroxy ketones by enantioselective oxidation of silyl enol ethers with a fructose-derived dioxirane , 1998 .

[18]  D. Enders,et al.  A Novel Asymmetric Benzoin Reaction Catalyzed by a Chiral Triazolium Salt. Preliminary communication , 1996 .

[19]  E. Dikici,et al.  New chiral synthon from the PLE catalyzed enantiomeric separation of 6-acetoxy-3-methylcyclohex-2-en-1-one , 1996 .

[20]  R. Schowen,et al.  Mechanism of the benzoin condensation , 1971 .

[21]  F. A. Davis,et al.  Asymmetric hydroxylation of enolates with N-sulfonyloxaziridines , 1992 .

[22]  C. Tanyeli,et al.  Synthesis and Rhizopus oryzae mediated enantioselective hydrolysis of α-acetoxy aryl alkyl ketones , 1998 .

[23]  L. Domingo,et al.  Postulation of bis(thiazolin-2-ylidene)s as the catalytic species in the benzoin condensation catalyzed by a thiazolium salt plus base , 1988 .

[24]  W. Adam,et al.  Synthesis of Optically Active α-Hydroxy Carbonyl Compounds by the Catalytic, Enantioselective Oxidation of Silyl Enol Ethers and Ketene Acetals with (Salen)manganese(III) Complexes , 1998 .

[25]  W. Adam,et al.  Kinetic resolution of racemic α-hydroxy ketones by lipase-catalyzed irreversible transesterification , 1996 .

[26]  D. Kingston,et al.  Synthesis of 10-deacetoxytaxol and 10-deoxytaxotere , 1993 .