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Urea‐ and Thiourea‐Substituted Cinchona Alkaloid Derivatives as Highly Efficient Bifunctional Organocatalysts for the Asymmetric Addition of Malonate to Nitroalkenes: Inversion of Configuration at C9 Dramatically Improves Catalyst Performance.
Author(s) -
McCooey Séamus H.,
Con Stephen J.
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.200501721
Subject(s) - thiourea , cinchona , bifunctional , malonate , chemistry , catalysis , enantioselective synthesis , organic chemistry , organocatalysis , urea , combinatorial chemistry
Natural not always best : Novel N ‐aryl urea and thiourea derivatives of dihydrocinchona alkaloids serve as efficient catalysts for the asymmetric addition of dimethyl malonate to a range of nitroalkenes. Catalytic activity and selectivity depend strongly on the relative configuration at C8/C9. Catalysts with “non‐natural” inverted configuration at C9 display excellent activity and enantioselectivity at loadings as low as 0.5 mol %.