Catalytic asymmetric cyanosilylation of ketones by a chiral amino acid salt

Xiaohua Liu; Bo Qin; Xin Zhou; Bin He; Xiaoming Feng

doi:10.1021/ja052629d

Catalytic asymmetric cyanosilylation of ketones by a chiral amino acid salt

J Am Chem Soc. 2005 Sep 7;127(35):12224-5. doi: 10.1021/ja052629d.

Authors

Xiaohua Liu¹, Bo Qin, Xin Zhou, Bin He, Xiaoming Feng

Affiliation

¹ Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P R China.

PMID: 16131191
DOI: 10.1021/ja052629d

Abstract

In this Communication, we describe the first highly enantioselective cyanosilylation of ketones catalyzed by simple chiral amino acid salt. A broad range of aromatic, alpha,beta-unsaturated, heterocyclic ketones catalyzed by l-phenylglycine sodium salt gave the corresponding trimethylsilyl ethers of cyanohydrins in 75-96% yields with 86-97% enantioselectivities. A catalytic cycle based on experimental phenomena and studies has been proposed to explain the origin of this activation. The reaction employed commercially available and fully recyclable catalysts and involves a simple experimental procedure.