☆ 4.8 Article

Discovery and Application of Doubly Quaternized Cinchona-Alkaloid-Based Phase-Transfer Catalysts

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Volume 53, Issue 32, Pages 8375-8378

Publisher

WILEY-V C H VERLAG GMBH

DOI: 10.1002/anie.201404084

Keywords

asymmetric synthesis; enantioselectivity; organocatalysis; phase-transfer catalysis; spiro compounds

Categories

Chemistry, Multidisciplinary

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Abstract

We report the discovery of novel N, N'-disubstituted cinchona alkaloids as efficient phase-transfer catalysts for the assembly of stereogenic quaternary centers. In comparison to traditional cinchona-alkaloid-based phase-transfer catalysts, these new catalysts afford substantial improvements in enantioselectivity and reaction rate for intramolecular spirocyclization reactions with catalyst loadings as low as 0.3 mol% under mild conditions.

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