The Journal of Organic Chemistry

Reaction of Phosphonate-Stabilized Carbanions with Cyclic Enones Bearing a. beta.-Leaving Group

MJ Mphahlele, TA Modro

Index: Mphahlele, Malose J.; Modro, Tomasz A. Journal of Organic Chemistry, 1995 , vol. 60, # 25 p. 8236 - 8240

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Citation Number: 31

Abstract

Reaction between a-lithiated alkylphosphonic esters and a, P-unsaturated cyclopentenones and cyclohexenones carrying a heteroatom substituent Y in the 8-position was studied. Complete chemoselectivity was observed as a function of substituent Y. For Y= OMe exclusive additionelimination at the/?-carbon was observed, yielding a, P-unsaturated d- ketophosphonates. The P-chloro-substituted substrates (Y= C1) derived from ...

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