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Chiral C 2 ‐Symmetric Cu II Complexes as Catalysts for Enantioselective Hetero‐Diels–Alder Reactions
Author(s) -
Evans David A.,
Olhava Edward J.,
Johnson Jeffrey S.,
Janey Jacob M.
Publication year - 1998
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/(sici)1521-3773(19981231)37:24<3372::aid-anie3372>3.0.co;2-k
Subject(s) - enantioselective synthesis , oxazoline , catalysis , chemistry , aryl , alkoxy group , diels–alder reaction , substrate (aquarium) , alkyl , medicinal chemistry , stereochemistry , organic chemistry , oceanography , geology
Air‐stable and recyclable , the Cu II –(bis)oxazoline complex 1 efficiently catalyzes diastereo‐ and enantioselective hetero‐Diels–Alder reactions between β , γ ‐unsaturated α ‐keto acid derivatives 2 and vinyl ethers for the synthesis of substituted dihydropyrans 3 [Eq. (1)]. Results of the crystal structure analysis of 1 in combination with calculations on model compounds indicate the formation of a reactive intermediate through replacement of the two H 2 O ligands with a chelating substrate. X=OEt, N(OMe)Me; R=alkyl, aryl, alkoxy, thiobenzyl.