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对映选择性膦催化混合茚与 MBH 碳酸酯的烯丙基烷基化反应。

Enantioselective Phosphine-Catalyzed Allylic Alkylations of mix-Indene with MBH Carbonates.

机构信息

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University , 3663 N. Zhongshan Road, Shanghai 200062, P. R. China.

出版信息

Org Lett. 2017 Nov 17;19(22):6080-6083. doi: 10.1021/acs.orglett.7b02895. Epub 2017 Oct 27.

Abstract

The first enantioenriched synthesis of 1,1,3-trisubstituted (trifluoromethyl)indene derivatives, bearing a quaternary stereogenic carbon center, is reported using a simple chiral sulfinamide phosphine-catalyzed asymmetric allylic alkylation of a mixture of indenes with Morita-Baylis-Hillman carbonates. The resulting derivatives can serve as a valuable synthetic building block for some drugs and natural products. Broad substrate scope and high regio- and enantioselectivity of this reaction were particularly remarkable.

摘要

首次报道了通过简单的手性亚砜胺-膦催化的混合茚与 Morita-Baylis-Hillman 碳酸酯的不对称烯丙基烷基化反应,实现了 1,1,3-三取代(三氟甲基)茚衍生物的对映体富集合成,其中带有季碳手性中心。所得衍生物可作为一些药物和天然产物的有价值的合成砌块。该反应具有广泛的底物范围和高度的区域和对映选择性,这一点尤为显著。

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