Enantioselective Synthesis of Cyclobutanes via Sequential Rh-catalyzed Bicyclobutanation/Cu-catalyzed Homoconjugate Addition

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• 作者：Robert Panish ; Srinivasa R. Chintala ; David T. Boruta ; Yinzhi Fang ; Michael T. Taylor ; Joseph M. Fox
• 刊名：The Journal of the American Chemical Society
• 出版年：2013
• 出版时间：June 26, 2013
• 年：2013
• 卷：135
• 期：25
• 页码：9283-9286
• 全文大小：350K
• 年卷期：v.135,no.25(June 26, 2013)
• ISSN：1520-5126

文摘

Enantiomerically enriched cyclobutanes are constructed by a three-component process in which t-butyl (E)-2-diazo-5-arylpent-4-enoates are treated with Rh₂(S-NTTL)₄ to provide enantiomerically enriched bicyclobutanes, which can subsequently engage in homoconjugate addition/enolate trapping sequence to give densely functionalized cyclobutanes with high diastereoselectivity. This three-component, two-catalyst procedure can be carried out in a single flask. Rh₂(S-NTTL)₄-catalyzed reaction of t-butyl (Z)-2-diazo-5-phenylpent-4-enoate gives the B眉chner cyclization product in excellent enantioselectivity.