Synthesis 2014; 46(05): 586-595
DOI: 10.1055/s-0033-1340787
short review
© Georg Thieme Verlag Stuttgart · New York

Recent Progress in the Asymmetric Intermolecular Halogenation of Alkenes

Jie Chen
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710069, P. R. of China   Fax: +86(29)88303915   Email: zhoul@nwu.edu.cn
,
Ling Zhou*
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710069, P. R. of China   Fax: +86(29)88303915   Email: zhoul@nwu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 22 December 2013

Accepted after revision: 20 January 2014

Publication Date:
31 January 2014 (online)


Abstract

As a long-standing problem in organic chemistry, and a very useful transformation in organic synthesis, the catalytic asymmetric halogenation of alkenes has only recently been reported. New catalysts and novel approaches have been developed for asymmetric halocyclizations. Although mechanism studies indicated the asymmetric intermolecular halogenation of alkenes is more difficult, important breakthroughs have also been achieved. In this review article, the scope, mechanism, and limitations of recently developed catalytic asymmetric intermolecular halogenation of alkenes are described.

1 Introduction

2 Asymmetric Intermolecular Halogenation of Alkenes

2.1 Asymmetric Halogenation of α,β-Unsaturated Compounds

2.2 Asymmetric Halogenation of Allylic Alcohols

2.3 Asymmetric Halogenation of Enecarbamates and Enamides

2.4 Asymmetric Halogenation of Allylic Sulfonamides

2.5 Asymmetric Halogenation of Unfunctionalized Alkenes

3 Summary and Outlook