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. | Zendy

McCooey Séamus H. | Zendy; Con Stephen J. | Zendy

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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 %.

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