Chiral Spiro Dienes Derived Boranes for Asymmetric Hydrosilylation of Ketones

doi:10.6023/cjoc201903076

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (8): 2257-2263.DOI: 10.6023/cjoc201903076 Previous Articles Next Articles

Special Issue: 陈茹玉先生诞辰100周年；元素有机化学合辑2018-2019；有机硅化学虚拟合辑

手性螺环骨架硼烷催化酮的不对称硅氢化反应

王桥天^a,b, 韩彩芳^a,b, 冯向青^a,b, 杜海峰^a,b

a 中国科学院化学研究所北京国家分子科学研究中心中国科学院分子识别与功能重点实验室北京 100190;
b 中国科学院大学北京 100049

收稿日期:2019-03-30 修回日期:2019-04-24 发布日期:2019-05-10
通讯作者: 冯向青, 杜海峰 E-mail:fxq@iccas.ac.cn;haifengdu@iccas.ac.cn
基金资助:
国家自然科学基金（No.21825108）资助项目.

Chiral Spiro Dienes Derived Boranes for Asymmetric Hydrosilylation of Ketones

Wang Qiaotian^a,b, Han Caifang^a,b, Feng Xiangqing^a,b, Du Haifeng^a,b

a Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190;
b University of Chinese Academy of Sciences, Beijing 100049

Received:2019-03-30 Revised:2019-04-24 Published:2019-05-10
Contact: 10.6023/cjoc201903076 E-mail:fxq@iccas.ac.cn;haifengdu@iccas.ac.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21825108).

1. Chiral Spiro Dienes Derived Boranes for Asymmetric Hydrosilylation of Ketones.PDF(6722KB)

Abstract

The chemistry of frustrated Lewis pairs (FLPs) is among the challenging frontiers of synthetic chemistry, which provides a powerful approach for metal-free catalytic hyrogenations and Piers-type hydrosilylations. In recent years, a significant progress has been made in this field. However, the deveopment of asymmetric reactions is still sluggish. The lacks of highly effective and enantioselective chiral FLP catalysts represent the key issue. C₂-symmetric 1,1'-spirobiindane is one privileged framework in chiral ligands and catalysts. On the basis of chiral binaphthyl diene-derived frustrated Lewis pairs (FLPs) developed by our group, in this work, we designed and synthesized a novel class of chiral spiro dienes, which could further react with Piers' borane via the hydroboration reaction to generate chiral boranes in situ. With the combination of chiral borane and tri-tert-butylphosphine as an FLP catalyst, an asymmetric Piers-type hydrosilylation of simple ketones was successfully realized to give the desired secondary alcohols with up to 90% ee.

Key words: asymmetric catalysis, asymmetric hydrosilylation, frustrated Lewis pairs, chiral spiro dienes, ketones

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Wang Qiaotian, Han Caifang, Feng Xiangqing, Du Haifeng. Chiral Spiro Dienes Derived Boranes for Asymmetric Hydrosilylation of Ketones[J]. Chin. J. Org. Chem., 2019, 39(8): 2257-2263.

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手性螺环骨架硼烷催化酮的不对称硅氢化反应

Chiral Spiro Dienes Derived Boranes for Asymmetric Hydrosilylation of Ketones

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