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Practical Access to 2‐Alkylsuccinates through Asymmetric Catalytic Hydrogenation of Stobbe‐Derived Itaconates
Author(s) -
Burk Mark J.,
Bienewald Frank,
Harris Michael,
ZanottiGerosa Antonio
Publication year - 1998
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/(sici)1521-3773(19980803)37:13/14<1931::aid-anie1931>3.0.co;2-3
Subject(s) - catalysis , cationic polymerization , rhodium , benzene , chemistry , asymmetric hydrogenation , catalytic hydrogenation , organic chemistry , medicinal chemistry , polymer chemistry , enantioselective synthesis
Enantiomerically pure 2‐alkylsuccinates are obtained on a 500‐g scale after hydrogenation with the cationic rhodium complexes with tetraalkyl‐substituted 1,2‐bis(phospholanyl)ethane or ‐benzene ligands [R′‐DuPHOS; Eq. (a)]. The catalysts allow smooth hydrogenation of mixtures of the prochiral E and Z isomers of itaconate derivatives with very high enantioselectivities and catalytic efficiencies; even tetrasubstituted itaconates were hydrogenated with 96% ee .