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Organocatalytic anti ‐Selective Mannich Reactions with Fluorinated Aldimines: Synthesis of anti ‐γ‐Fluoroalkyl‐γ‐amino Alcohols
Author(s) -
Fustero Santos,
Mojarrad Fatemeh,
Carrión María Dolores Pérez,
SanzCervera Juan F.,
Aceña José Luis
Publication year - 2009
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.200900509
Subject(s) - aldimine , chemistry , organic chemistry , mannich reaction , organocatalysis , alkyl , trimethylsilyl , adduct , ether , catalysis , enantioselective synthesis
The asymmetric Mannich reaction between fluoroalkyl aldimines and aldehydes catalyzed by α,α‐diphenylprolinol trimethylsilyl ether is reported. The corresponding Mannich adducts were reduced in situ to afford anti ‐β‐alkyl‐γ‐fluoroalkyl‐γ‐amino alcohols in moderate yields and with very high diastereo‐ and enantioselectivities. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)