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Frontispiece: Catalytic Asymmetric Bromination of Unfunctionalized Olefins with H 2 O as a Nucleophile
Author(s) -
Zhang Xun,
Li Jing,
Tian Hua,
Shi Yian
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201583361
Subject(s) - halogenation , nucleophile , cinchona , bromine , chemistry , optically active , catalysis , enantioselective synthesis , organic chemistry , cinchona alkaloids , polymer chemistry
Asymmetric Bromohydroxylation The formation of halohydrins via halonium ion intermediates with H 2 O is a classic route to the halogenation of olefins and has great synthetic value. An asymmetric version of this process is thus highly desirable. The dimeric cinchona alkaloid (DHQD) 2 PHAL has been used to catalyze an effective asymmetric bromohydroxylation of unfunctionalized olefins with H 2 O as nucleophile and N ‐bromobenzamide as a bromine source, as discussed by Y. Shi et al. in their Commmunication on page 11658 ff. , affording a variety of optically active bromohydrins with up to 88 % ee.