Organic letters

Stereoselective Synthesis of Dienyl Phosphonates via Extended Tethered Ring-Closing Metathesis

B Schmidt, O Kunz

Index: Schmidt, Bernd; Kunz, Oliver Organic Letters, 2013 , vol. 15, # 17 p. 4470 - 4473

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Citation Number: 8

Abstract

Allylphosphonates of allylic alcohols were converted to conjugated dienyl phosphonates in a one-flask reaction, comprising a ring-closing metathesis (RCM), a base-induced ring- opening, and an alkylation. The ring-opening proceeds with very high diastereoselectivity, giving exclusively the (1 Z, 3 E)-configured dienes. Single diastereomers and mixtures of diastereomers can be used as starting materials without noticeable effect on the ...