Stereoselective synthesis of chiral α-amino-β-lactams through palladium(II)-catalyzed sequential monoarylation/amidation of C(sp(3) )-H bonds

Qi Zhang; Kai Chen; Weihao Rao; Yuejun Zhang; Fa-Jie Chen; Bing-Feng Shi

doi:10.1002/anie.201306625

Stereoselective synthesis of chiral α-amino-β-lactams through palladium(II)-catalyzed sequential monoarylation/amidation of C(sp(3) )-H bonds

Angew Chem Int Ed Engl. 2013 Dec 16;52(51):13588-92. doi: 10.1002/anie.201306625. Epub 2013 Oct 31.

Authors

Qi Zhang¹, Kai Chen, Weihao Rao, Yuejun Zhang, Fa-Jie Chen, Bing-Feng Shi

Affiliation

¹ Department of Chemistry, Zhejiang University, Hangzhou 310027 (China) http://mypage.zju.edu.cn/bfshi.

PMID: 24174011
DOI: 10.1002/anie.201306625

Abstract

Give Me an Ar, give Me an N! Arylation of the methyl group in a simple derivative of readily available alanine under palladium catalysis was followed by intramolecular amidation at the same position to give chiral α-amino-β-lactams with a wide range of aryl substituents (see scheme; Phth=phthaloyl). The α-amino-β-lactams were obtained in moderate to high yields with good functional-group tolerance and high diastereoselectivity.

Keywords: CH activation; amidation; arylation; palladium; β-lactams.

Publication types

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

MeSH terms

Catalysis
Molecular Structure
Palladium / chemistry*
Stereoisomerism
beta-Lactams / chemical synthesis*
beta-Lactams / chemistry

Substances

beta-Lactams
Palladium