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Enantioselective Organocatalytic Conjugate Addition of Fluorocarbon Nucleophiles to α,β‐Unsaturated Aldehydes
Author(s) -
Ullah Farman,
Zhao GuiLing,
Deiana Luca,
Zhu Mingzhao,
Dziedzic Pawel,
Ibrahem Ismail,
Hammar Peter,
Sun Junliang,
Córdova Armando
Publication year - 2009
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.200901260
Subject(s) - enantioselective synthesis , nucleophile , fluorocarbon , fluorine , conjugate , chemistry , optically active , organocatalysis , combinatorial chemistry , catalysis , organic chemistry , mathematics , mathematical analysis
A highly chemo‐ and enantioselective organocatalytic addition of fluorocarbon nucleophiles, such as 1‐fluoro‐bis(phenylsulfonyl)methane, to α,β‐unsaturated aldehydes is presented (see scheme). The reactions are catalyzed by simple chiral amines and give access to optically active fluorine derivatives in good yields and up to 95 % ee. Notably, the methodology can be applied to the formation of a chiral quaternary carbon center bearing a fluorine atom with high enantioselectivity.