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三氟甲磺酸铋催化对醌甲腙与 3-丙烯基-2-硅氧基吲哚的烯丙基亲核 1,6-共轭加成。

Bismuth Triflate-Catalyzed Vinylogous Nucleophilic 1,6-Conjugate Addition of para-Quinone Methides with 3-Propenyl-2-silyloxyindoles.

机构信息

State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, College of Chemistry, Nankai University , Tianjin 300071, P. R. China.

出版信息

Org Lett. 2017 Dec 15;19(24):6708-6711. doi: 10.1021/acs.orglett.7b03433. Epub 2017 Nov 28.

Abstract

A highly diastereoselective vinylogous nucleophilic 1,6-conjugate addition reaction of para-quinone methides with 3-propenyl-2-silyloxyindoles by a bismuth triflate catalyst has been developed. A number of diphenylmethane type compounds functionalized with oxindole motifs was obtained with excellent yields (up to 99%) and very good diastereoselectivities (up to Z/E > 99:1).

摘要

发展了一种由三氟甲磺酸铋催化剂促进的对醌甲亚胺与 3-丙烯基-2-硅氧基吲哚的高非对映选择性的烯醇式亲核 1,6-共轭加成反应。通过该反应得到了许多带有氧化吲哚结构的二苯甲烷类化合物,收率高(高达 99%),非对映选择性好(高达 Z/E>99:1)。

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