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Asymmetric Mannich Reaction of Fluorinated Ketoesters with a Tryptophan‐Derived Bifunctional Thiourea Catalyst
Author(s) -
Han Xiao,
Kwiatkowski Jacek,
Xue Feng,
Huang KuoWei,
Lu Yixin
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200903635
Subject(s) - stereocenter , bifunctional , mannich reaction , vicinal , catalysis , chemistry , thiourea , tryptophan , combinatorial chemistry , organic chemistry , enantioselective synthesis , stereochemistry , amino acid , biochemistry
Fluorinated quaternary stereocenters : A novel bifunctional catalyst 1 derived from natural tryptophan promoted the Mannich reaction of α‐fluoro‐β‐ketoesters to afford fluorinated chiral molecules containing vicinal quaternary and tertiary stereogenic centers with exceptional enantioselectivity. An unprecedented α‐fluoro‐β‐lactam was also prepared by this method (see scheme; Boc= tert ‐butoxycarbonyl).