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Asymmetric dihydroxylation of 1-acyloxy-2(E)-alkenylphosphonates with AD-mix reagents. Effects of 1-acyloxy functional groups on the asymmetric dihydroxylation

โœ Scribed by Tsutomu Yokomatsu; Takehiro Yamagishi; Tomoyuki Sada; Kenji Suemune; Shiroshi Shibuya

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

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โœฆ Synopsis

Asymmetric dihydroxylation (AD) of a racemic mixture of 1-acyloxy-2(E)-alkenylphosphonates with AD-mix-ot or -I] reagents was examined. The kinetic rate of dihydroxylation was highly dependent upon the configuration of the 1-acyioxy functional group as well as the nature of substituents at the 3-position. The reaction of a racemic mixture of diethyl (E)-3-phenyl-l-acetyloxy-2-propenylphosphonate with an AD-ra/x-13 reagent preferentially dihydroxylated the R-enantiomer to leave an unreacted S-enantiomer of high enantiomeric purity. Double diastereoselection of the resolved diethyl 3-phenyl-l-acetyloxy-2(E)-propenylphosphonate in dihydroxylation was also examined.

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