Asymmetric bromolactonization using amino-thiocarbamate catalyst

Ling Zhou; Chong Kiat Tan; Xiaojian Jiang; Feng Chen; Ying-Yeung Yeung

doi:10.1021/ja1048972

Asymmetric bromolactonization using amino-thiocarbamate catalyst

J Am Chem Soc. 2010 Nov 10;132(44):15474-6. doi: 10.1021/ja1048972.

Authors

Ling Zhou¹, Chong Kiat Tan, Xiaojian Jiang, Feng Chen, Ying-Yeung Yeung

Affiliation

¹ Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.

PMID: 20945837
DOI: 10.1021/ja1048972

Abstract

A novel amino-thiocarbamate-catalyzed bromolactonization of unsaturated carboxylic acids has been developed. The scope of the reaction is evidenced by 22 examples of γ-lactones with up to 99% yield and 93% ee. The protocol was applied in the enantioselective synthesis of the key intermediates of VLA-4 antagonists.