Synthesis of nonracemic allylic hydroxy phosphonates via alkene cross metathesis

A He, B Yan, A Thanavaro, CD Spilling…

Index: He, Anyu; Yan, Bingli; Thanavaro, Anchalee; Spilling, Christopher D.; Rath, Nigam P. Journal of Organic Chemistry, 2004 , vol. 69, # 25 p. 8643 - 8651

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Citation Number: 31

Abstract

Allylic hydroxy phosphonates and their derivatives can be interconverted by using cross metathesis with second generation Grubbs catalyst. The absolute stereochemistry of the starting phosphonate is conserved in the product. Cross metathesis reaction of the acrolein- derived phosphonate 2a yields a series of functionalized allylic hydroxy phosphonates. However, the cross metathesis reaction is often accompanied by competing dimerization ...