Catalytic Asymmetric Bromination of Unfunctionalized Olefins with H2O as a Nucleophile

Xun Zhang; Jing Li; Hua Tian; Yian Shi

doi:10.1002/chem.201502133

Catalytic Asymmetric Bromination of Unfunctionalized Olefins with H2O as a Nucleophile

Chemistry. 2015 Aug 10;21(33):11658-63. doi: 10.1002/chem.201502133. Epub 2015 Jul 2.

Authors

Xun Zhang¹, Jing Li¹, Hua Tian¹, Yian Shi^{2

3

4}

Affiliations

¹ Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 10090 (P. R. China).
² Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 10090 (P. R. China). Yian.Shi@colostate.edu.
³ State Key Laboratory of Coordination Chemistry, Center for Multimolecular Organic Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (P. R. China). Yian.Shi@colostate.edu.
⁴ Department of Chemistry, Colorado State University, Fort Collins, Colorado, 80523 (USA). Yian.Shi@colostate.edu.

PMID: 26137926
DOI: 10.1002/chem.201502133

Abstract

The dimeric cinchona alkaloid (DHQD)2 PHAL is used to catalyze an effective asymmetric bromohydroxylation of unfunctionalized olefins with H2 O as nucleophile an N-bromobenzamide as a bromine source. A variety of optically active bromohydrins are formed with up to 88 % ee.

Keywords: bromination; cinchona alkaloids; enantioselectivity; olefins; water.