New chiral building blocks by microbial asymmetric reduction: A direct access to functionalized 2R,3R- and 2S,3R-2-methyl-3-hydroxy butyrate synthons

doi:10.1016/S0040-4039(00)96688-7

Tetrahedron Letters

Volume 28, Issue 42, 1987, Pages 5033-5036

https://doi.org/10.1016/S0040-4039(00)96688-7 Get rights and content

Abstract

The Reduction of 4-O-benzyl-2 -methyl-3-oxo-butyrate esters by several fungal strains produces predominantly (2S,3R)- $anti$ -hydroxyesters in high optical purity. The corresponding (2R,3R)- $syn$ isomer was obtained, with other strains, only in mixture with the $anti$ isomer. These esters are useful precursors for chiral 2-methyl-3-hydroxy-butyrolactone synthons.

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A series of 2-oxoalkanephosphonates 2 were screened for reduction with Geotrichum candidum. Only diethyl 2-oxopropanephosphonate 2a underwent asymmetric reduction to give (+)-(R)-diethyl 2-hydroxypropanephosphonate 3a with 98% e.e. In turn, a series of racemic 2-hydroxyalkanephosphonates 3 were acetylated under kinetic resolution conditions in the presence of various lipases to give the corresponding 2-acetoxyalkanephosphonates 4 and recovered alcohols 3 in good yields and with e.e. up to 93%.
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^☆: This work was presented in part at the IVth European Symposium of Organic Chemistry, Aix-en-Provence (France), Sept. 1985

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New chiral building blocks by microbial asymmetric reduction: A direct access to functionalized 2R,3R- and 2S,3R-2-methyl-3-hydroxy butyrate synthons☆

Abstract

Tetrahedron Lett.

Tetrahedron Lett.

Chem. Pharm. Bull.

Synthesis

Synthesis

J. Chromatogr.

Chem. Pharm. Bull.

Chem. Pharm. Bull.

Chem. Pharm. Bull.

Tetrahedron Lett.