Highly Enantioselective Diels-Alder Reaction of a Photochemically Generated o-Quinodimethane with Olefins

Four stereogenic centers in one step are established with almost perfect control of the absolute and relative configuration in a photochemically induced Diels–Alder reaction of substrate 1 and dimethyl fumarate. The carrier of the chiral information, lactam 2, fixes the substrate by hydrogen bonds i...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2003-08, Vol.42 (31), p.3693-3696
Main Authors: Grosch, Benjamin, Orlebar, Caroline N., Herdtweck, Eberhardt, Massa, Werner, Bach, Thorsten
Format: Article
Language:English
Subjects:
asymmetric syntheses
Diels-Alder reaction
enantioselectivity
enols
photochemistry
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Summary:Four stereogenic centers in one step are established with almost perfect control of the absolute and relative configuration in a photochemically induced Diels–Alder reaction of substrate 1 and dimethyl fumarate. The carrier of the chiral information, lactam 2, fixes the substrate by hydrogen bonds in a chiral environment and in this way controls the configuration of the stereogenic centers of product 3.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200351567