Conjugate addition of 2-and 4-pyridylcuprates: an expeditious asymmetric synthesis of natural (-)-evoninic acid

AC Spivey, L Shukla, JF Hayler

Index: Spivey, Alan C.; Shukla, Lena; Hayler, Judy F. Organic Letters, 2007 , vol. 9, # 5 p. 891 - 894

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Citation Number: 29

Abstract

The scope and limitations of the conjugate addition of 2-and the first 4-pyridyl Gilman homocuprates to various α, β-unsaturated Michael acceptors are delineated. The conjugate addition of the cuprate of 2-bromo-3-methylpyridine to (E)-methyl crotonate then diastereoselective enolate alkylation and lipase-mediated enantioselective ester hydrolysis have enabled an efficient four-step first asymmetric synthesis of the Celastraceae ...