Synfacts 2006(9): 0952-0952  
DOI: 10.1055/s-2006-949228
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

A Phosphoramide Catalyzed Asymmetric Diels-Alder Reaction

Contributor(s): Benjamin List, Sebastian Hoffmann
D. Nakashima, H. Yamamoto*
University of Chicago, USA
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Publikationsverlauf

Publikationsdatum:
23. August 2006 (online)

Significance

An organocatalyzed asymmetric Diels-Alder reaction of ethyl vinyl ketone with silyl­oxydiene is described. For this purpose, the authors have developed a N-triflyl phosphoramide as a strong chiral Brønsted acid catalyst. This chiral catalyst allows the activation of unsaturated ketones, leading to substituted cyclohexene derivatives in moderate to good yields and good enantioselectivities.