Highly Diastereo‐ and Enantioselective Organocatalytic One‐Pot Sequential 1,4‐Addition/Dearomative‐Fluorination Transformation | Zendy

Li Feng | Zendy; Sun Long | Zendy; Teng Yuou | Zendy; Yu Peng | Zendy; Zhao John CongGui | Zendy; Ma JunAn | Zendy

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Highly Diastereo‐ and Enantioselective Organocatalytic One‐Pot Sequential 1,4‐Addition/Dearomative‐Fluorination Transformation

Author(s) -

Li Feng,

Sun Long,

Teng Yuou,

Yu Peng,

Zhao John CongGui,

Ma JunAn

Publication year - 2012

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.201202636

Subject(s) - stereocenter , enantioselective synthesis , electrophilic fluorination , chemistry , transformation (genetics) , tertiary amine , electrophile , thiourea , yield (engineering) , amine gas treating , catalysis , organic chemistry , combinatorial chemistry , materials science , biochemistry , metallurgy , gene

Fluorination : A wide range of nitroolefins and pyrazol‐5‐ones undergo a sequential 1,4‐addition/dearomative‐fluorination transformation when treated with a catalytic amount of a tertiary‐amine—thiourea compound and the terminal electrophile, N ‐fluorobenzenesulfonimide, to give fluorinated products in 72–95 % yield with up to 99:1 d.r. and 98 % ee. Notably, these products contain adjacent tertiary and α‐fluoro quaternary stereocenters (see scheme).

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