Tetrahedron Letters

Generation of allyl Grignard reagents via titanocene-catalyzed activation of allyl halides

LM Fleury, BL Ashfeld

Index: Fleury, Lauren M.; Ashfeld, Brandon L. Tetrahedron Letters, 2010 , vol. 51, # 18 p. 2427 - 2430

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Citation Number: 20

Abstract

A protocol for the generation of allyl Grignard reagents via the catalytic activation of allyl halides is described herein. Subsequent nucleophilic addition to carbonyl derivatives provided the desired homo allylic alcohols in excellent yields (84–99%). Evidence suggests that titanocene dichloride catalyzes the formation of an allyl Grignard species which reacts solely with the carbonyl electrophile as evidenced by the complete absence of Würtz ...