Intramolecularly competitive Ireland-Claisen rearrangements: Scope and potential applications to natural product synthesis

…, T Yaramasu, X Zhang, MC McIntosh

Index: Hong, Sang-Phyo; Lindsay, Harriet A.; Yaramasu, Tripura; Zhang, Xiaowei; McIntosh, Matthias C. Journal of Organic Chemistry, 2002 , vol. 67, # 7 p. 2042 - 2055

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Citation Number: 32

Abstract

A variety of bis-allylic esters were prepared by vinylmetal addition to cycloalkenones followed by esterification either in situ or in a separate operation. For chiral cyclohexenones, the vinyl additions generally occurred with> 10: 1 diastereoselectivity. Although in some cases the bis-allylic esters proved to be sensitive to silica gel or other adsorbents, all of the esters examined could be isolated in acceptable purity. The Ireland-Claisen ...