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α-烷基烯醇盐的催化直接型取代反应:一种钯/布朗斯特碱催化的磺酰亚胺脱羧烯丙基化方法。

Catalytic direct-type substitution reaction of alpha-alkyl enolates: a Pd/Brønsted base-catalysed approach to the decarboxylative allylation of sulfonylimidates.

作者信息

Kan S B Jennifer, Matsubara Ryosuke, Berthiol Florian, Kobayashi Shū

机构信息

Department of Chemistry, School of Science and Graduate School of Pharmaceutical Sciences, The University of Tokyo, The HFRE Division, ERATO, Japan Science Technology Agency, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.

出版信息

Chem Commun (Camb). 2008 Dec 21(47):6354-6. doi: 10.1039/b815845b. Epub 2008 Oct 29.

Abstract

A mild and efficient process for the direct-type catalytic allylation of sulfonylimidates has been developed; this reaction represents the first example of Brønsted base-catalysed, in situ generation and use of alpha-alkyl enolates in substitution reactions; the success of this methodology stems from the tunable alpha-proton acidity and nucleophilicity of sulfonylimidates, which could be harnessed in the realization of a broader range of catalytic direct-type reactions using ester equivalents as nucleophiles.

摘要

已开发出一种温和且高效的用于磺酰亚胺直接型催化烯丙基化的方法;该反应代表了布朗斯特碱催化、原位生成并在取代反应中使用α-烷基烯醇盐的首个实例;该方法的成功源于磺酰亚胺可调节的α-质子酸度和亲核性,这可用于实现以酯当量作为亲核试剂的更广泛的催化直接型反应。

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