A stereoselective synthesis of functionalized alkenyllithiums and alkenyl cyanocuprates by the copper (I)-catalyzed coupling of organolithium reagents with. alpha.- …

P Kocienski, S Wadman, K Cooper

Index: Kocienski, Philip; Wadman, Sjoerd; Cooper, Kelvin Journal of the American Chemical Society, 1989 , vol. 111, # 6 p. 2363 - 2365

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Citation Number: 103

Abstract

5 6 82% orcilll 2 97%(E 78% ovcnll. 2 97%(0 cyclic enol ethers with organolithium and Grignard reagents which result in ring cleavage via an apparent nucleophilic displacement. For example, 3, 4-dihydro-2H-pyran (1) reacts with primary alkyl and aryl Grignard reagents to give alkenols 2 in modest yield (eq A similar reaction occurs on treatment of 1 with alkyllithiums n