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