Highly Enantioselective and Regioselective Conjugate Addition of Nitromethane to 1,5-Diarylpenta-2,4-dien-1-ones Using Bifunctional Cinchona Organocatalysts

abstract

A general and efficient asymmetric organocatalytic 1,4-Michael addition of nitromethane to 1,5-diarylpenta-2,4-dien-1-ones (cinnamylideneacetophenones) catalyzed by 9-thiourea-9-(deoxy)-epi-hydroquinine has been developed. The reactions afforded excellent enantioselectivities (up to 99%), high yields ( up to 97%), and exclusive regioselectivity.

keywords

ASYMMETRIC MICHAEL ADDITION; QUATERNARY AMMONIUM-SALTS; ALPHA,BETA-UNSATURATED KETONES; PHASE-TRANSFER; THIOUREA ORGANOCATALYST; BOND DONORS; CATALYSIS; CHALCONES; ENONES; 9-AMINO-9-DEOXYEPIQUININE

subject category

Chemistry

authors

Oliva, CG; Silva, AMS; Paz, FAA; Cavaleiro, JAS

our authors

acknowledgements

Thanks are due to the University of Aveiro, to 'Fundacao para a Ciencia e a Tecnologia' and FEDER for funding the Organic Chemistry Research Unit and for the financial support towards the purchase of the single-crystal diffractometer. The authors are very grateful to Professor Juan Carlos Carretero (Universidad Autonoma de Madrid, Spain) for providing access and information on the use of chiral HPLC columns and also to Dr. Fernando Domingues (Universidade de Aveiro) for assistance in the HPLC determinations.

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