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Desymmetrization of Bisallylic Amides through Catalytic Enantioselective Bromocyclization with BINAP Monoxide
Author(s) -
Nagao Yoshihiro,
Hisanaga Tatsunari,
Egami Hiromichi,
Kawato Yuji,
Hamashima Yoshitaka
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201704847
Subject(s) - desymmetrization , enantioselective synthesis , stereocenter , alkene , oxazoline , binap , chemistry , moiety , stereoselectivity , monoxide , catalysis , stereochemistry , carbon monoxide , organic chemistry
We report the first desymmetrization of bisallylic amides by enantioselective bromocyclization with BINAP monoxide as a catalyst. Depending upon the substitution pattern of the alkene moieties, densely functionalized, optically active oxazoline or dihydrooxazine compounds were obtained in a highly stereoselective manner. The remaining alkene moiety was subjected to various functional group manipulations to afford a diverse array of chiral molecules with multiple stereogenic centers.