Journal of the American Chemical Society

A general preparative method for. alpha.-lithioethers and its application to a concise, practical synthesis of brevicomin

T Cohen, JR Matz

Index: Cohen, Theodore; Matz, James R. Journal of the American Chemical Society, 1980 , vol. 102, # 22 p. 6900 - 6902

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Citation Number: 153

Abstract

Until recently, a-lithioethers were nearly always prepared by deprotonation of an a-carbon atom of an ether which has a special anion-stabilizing feature. Examples of the latter are substituents such as carbonyl,'cyano, 2 phenylthi~,~ or most commonly carbon-carbon un~ aturation;~ in addition, sp2 hybridization of the ether carbon atom allows ready deprotonation by alkyllithiums even when anion-stabilizing substituents are ab~ ent.~ ...