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Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of 1(E)-alkenylphosphonates with AD-mix reagents

✍ Scribed by Tsutomu Yokomatsu; Takehiro Yamagishi; Kenji Suemune; Yoshinori Yoshida; Shiroshi Shibuya

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
969 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

Asymmetric dihydroxylation (AD) of 1 (E)-alkenylphosphonates with an AD-m/x -ct or -~ reagent was examined to give a series of optically active threo-ot,~-dihydroxyphosphonates. Good enantioselectivity (>88% ee) was observed in the AD reaction of l(E)-alkenylphosphonates with conjugated aromatic substituents. The steric effects of the ester functionality in the course of the dihydroxylation were also evaluated. Enantioselectivity and yield were significantly improved when the AD reaction was carried out with dimethyl phosphonate instead of diethyl phosphonate.

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