Tetrahedron: Asymmetry

The synthesis of 1-hydroxy phosphonates of high enantiomeric excess using sequential asymmetric reactions: titanium alkoxide-catalyzed P C bond formation and …

BJ Rowe, CD Spilling

Index: Rowe, Bradley J.; Spilling, Christopher D. Tetrahedron Asymmetry, 2001 , vol. 12, # 12 p. 1701 - 1708

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Citation Number: 69

Abstract

Titanium alkoxide-catalyzed asymmetric phosphonylation of aldehydes yields hydroxy phosphonates in moderate to good enantiomeric excess (ees∼ 70%). The hydroxy phosphonates were acetylated and the acetates were subjected to enzyme-catalyzed kinetic resolution. The non-racemic acetates 2 (predominantly (R)-enantiomer) were hydrolyzed with an (R)-enantiomer-selective lipase, resulting predominantly in the hydrolysis of the (R ...