Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
A Partial Asymmetric Synthesis via a Cyclic Oxyphosphorane
Motoo MuroiYuzo InouyeMinoru Ohno
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1969 Volume 42 Issue 10 Pages 2948-2951


A partial asymmetric synthesis was achieved in the carbon-carbon condensation which involved the reaction of (−)-menthyl pyruvate with trimethyl phosphite, followed by alkaline hydrolysis of the intermediate cyclic oxyphosphorane to yield (−)-(S:S)-2,3-dimethyltartaric acid. With knowledge of absolute configurations of both the chiral center and the predominant enantiomer of the product, an ex post facto interpretation of the steric course was made on the basis of relative steric stability of transition state conformations of the addition step of III to I.

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