Enantioselective synthesis of 4-substituted 4,5-dihydro-1H-[1,5]benzodiazepin-2(3H)-ones by the Lewis base-catalyzed hydrosilylation

Xing Chen; Yongsheng Zheng; Chang Shu; Weicheng Yuan; Bo Liu; Xiaomei Zhang

doi:10.1021/jo201334n

Enantioselective synthesis of 4-substituted 4,5-dihydro-1H-[1,5]benzodiazepin-2(3H)-ones by the Lewis base-catalyzed hydrosilylation

J Org Chem. 2011 Nov 4;76(21):9109-15. doi: 10.1021/jo201334n. Epub 2011 Oct 7.

Authors

Xing Chen¹, Yongsheng Zheng, Chang Shu, Weicheng Yuan, Bo Liu, Xiaomei Zhang

Affiliation

¹ Key Laboratory for Asymmetric Synthesis and Chiraltechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.

PMID: 21958202
DOI: 10.1021/jo201334n

Abstract

Enantioselective synthesis of 4-substituted 4,5-dihydro-1H-[1,5]benzodiazepin-2(3H)-ones has been accomplished through chiral Lewis base-catalyzed hydrosilylation. The corresponding products were obtained in excellent yields (up to 99%) and enantioselectivities (up to 98%). The absolute configuration of product 3n has been determined as S by X-ray crystallographic analysis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzodiazepines / chemical synthesis*
Benzodiazepines / chemistry*
Catalysis
Crystallography, X-Ray
Lewis Bases / chemistry*
Molecular Structure
Silanes / chemistry*
Stereoisomerism

Substances

Lewis Bases
Silanes
Benzodiazepines