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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).