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Highly Enantioselective Diels–Alder Reaction of a Photochemically Generated o ‐Quinodimethane with Olefins
Author(s) -
Grosch Benjamin,
Orlebar Caroline N.,
Herdtweck Eberhardt,
Massa Werner,
Bach Thorsten
Publication year - 2003
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.200351567
Subject(s) - stereocenter , enantioselective synthesis , substrate (aquarium) , chemistry , absolute configuration , hydrogen bond , diels–alder reaction , stereochemistry , organic chemistry , catalysis , molecule , oceanography , geology
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 .