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Carbometalation-Carboxylation of 2,3-Allenols with Carbon Dioxide: A Dramatic Effect of Halide Anion

Suhua Li, Bukeyan Miao, Weiming Yuan and Shengming Ma*

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. China, Email: masmsioc.ac.cn

S. Li, B. Miao, W. Yuan, S. Ma, Org. Lett., 2013, 15, 977-979.

DOI: 10.1021/ol4000197 (free Supporting Information)


Abstract

Cyclic organometallic intermediates formed via CuCl-mediated highly regio- and stereoselective carbomagnesiation of 2,3-allenols with Grignard reagents smoothly react with carbon dioxide to afford 2(5H)-furanones. The reaction with organomagnesium chlorides proceeded smoothly under mild conditions to afford the products in very good yields due a dramatic effect of the halide anion from the Grignard reagent for CO2 activation.

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A palladium catalyzed efficient synthesis of γ-methylene-α,β-unsaturated γ-lactones via cyclization of 3,4-alkadienoic acids

S. Ma, F. Yu, Tetrahedron, 2005, 61, 9896-9901.


Key Words

Butenolides


ID: J54-Y2013-0500