Desymmetrization of Bisallylic Amides through Catalytic Enantioselective Bromocyclization with BINAP Monoxide | Zendy

Nagao Yoshihiro | Zendy; Hisanaga Tatsunari | Zendy; Egami Hiromichi | Zendy; Kawato Yuji | Zendy; Hamashima Yoshitaka | Zendy

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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.

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