1-Bromo-1-lithioethene: A Practical Reagent for the Efficient Preparation of 2-Bromo-1-alken-3-ols

YY Novikov, P Sampson

Index: Novikov, Yehor Y.; Sampson, Paul Organic Letters, 2003 , vol. 5, # 13 p. 2263 - 2266

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Citation Number: 11

Abstract

A reliable preparative-scale synthesis of 1-bromo-1-lithioethene is reported. This reagent undergoes clean 1, 2-addition with a range of aldehydes and ketones at-105° C to afford the corresponding 2-bromo-1-alken-3-ols in moderate to excellent yield. Efficient diastereoselective addition to α-siloxy and α-methylcyclohexanones, as well as protected 3- keto furanose sugars, is achieved in the presence of 10 mol% CeBr3. The resulting ...