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Synthesis of Chiral α‐Fluoroketones through Catalytic Enantioselective Decarboxylation
Author(s) -
Nakamura Masaharu,
Hajra Alakananda,
Endo Kohei,
Nakamura Eiichi
Publication year - 2005
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.200502703
Subject(s) - enantioselective synthesis , stereocenter , chemistry , decarboxylation , racemization , chirality (physics) , substituent , palladium , total synthesis , asymmetric carbon , ligand (biochemistry) , stereochemistry , combinatorial chemistry , chiral ligand , kinetic resolution , catalysis , organic chemistry , optically active , biochemistry , nambu–jona lasinio model , chiral symmetry breaking , physics , receptor , quantum mechanics , quark
A conceptually new approach affords optically active α‐fluoroketones 3 in high yields with up to 99 % ee from racemic α‐fluoro‐β‐ketoesters 1 in the presence of a chiral phosphinooxazoline ligand 2 . The palladium‐catalyzed decarboxylation/allylation reaction also allows the highly enantioselective construction of an all‐carbon quaternary center. dba=dibenzylideneacetone.