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Highly Enantioselective Addition of 1‐Fluoro‐1‐nitro(phenylsulfonyl)methane to α,β‐Unsaturated Aldehydes
Author(s) -
Kamlar Martin,
Bravo Natalia,
Alba AndreaNekane R.,
Hybelbauerová Simona,
Císařová Ivana,
Veselý Jan,
Moyano Albert,
Rios Ramon
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000851
Subject(s) - enantioselective synthesis , chemistry , nitro , diastereomer , methane , organocatalysis , absolute configuration , catalysis , organic chemistry , medicinal chemistry , alkyl
An organocatalytic, highly enantioselective addition of 1‐fluoro‐1‐nitro(phenylsulfonyl)methane to α,β‐unsaturated aldehydes is reported. The reaction is simply catalyzed by secondary amines and furnishes the corresponding fluorinated derivatives in good yields, with moderate diastereoselectivities and excellent enantioselectivities. The absolute configuration of the major diastereomers was unambiguously ascertained by X‐ray diffraction analysis.
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