Asymmetric Synthesis of Silicon-Stereogenic Silanes by Copper-Catalyzed Desymmetrizing Protoboration of Vinylsilanes.,Angewandte Chemie International Edition

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Asymmetric Synthesis of Silicon-Stereogenic Silanes by Copper-Catalyzed Desymmetrizing Protoboration of Vinylsilanes.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-04-16 , DOI: 10.1002/anie.202005341
Ge Zhang ₁ , Yanfei Li ₁ , Ying Wang ₁ , Qian Zhang ₁ , Tao Xiong ₁ , Qian Zhang _{1,

2}

Affiliation

The catalytic asymmetric creation of silanes with silicon stereocenters is a long‐sought but underdeveloped topic, and only a handful of examples have been reported. Moreover, the construction of chiral silanes containing (more than) two stereocenters is a more arduous task and remains unexploited. We herein report an unprecedented copper‐catalyzed desymmetrizing protoboration of divinyl‐substituted silanes with bis(pinacolato)diboron (B₂pin₂). This method enables the facile preparation of an array of enantiomerically enriched boronate‐substituted organosilanes bearing contiguous silicon and carbon stereocenters with exclusive regioselectivity and generally excellent diastereo‐ and enantioselectivity.

中文翻译：

通过铜催化的乙烯基硅烷的不对称原硼烷基化反应不对称合成硅立体异构硅烷。

具有硅立构中心的硅烷催化不对称生成反应是一个长期存在但尚未开发的课题，仅报道了少数实例。而且，包含（多个）两个立体中心的手性硅烷的构建是一项艰巨的任务，并且尚未被开发。我们在本文中报道了前所未有的铜催化双乙烯基取代硅烷与双（频哪醇）双硼（B ₂ pin ₂）的原对称化。该方法可以轻松制备一系列具有对映异构体富集的硼酸酯取代的有机硅烷，这些有机硅烷带有连续的硅和碳立体中心，具有独特的区域选择性，并且通常具有出色的非对映和对映选择性。

更新日期：2020-04-16

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