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Enantioselective Diels–Alder Cycloaddition by Preorganization on a Chiral Lewis Acid Template
Author(s) -
Bienaymé Hugues
Publication year - 1997
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199726701
Subject(s) - enantioselective synthesis , cycloaddition , diels–alder reaction , lewis acids and bases , alder , chemistry , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , biology , botany
The key to success in asymmetric Diels–Alder cycloadditions may be the preorganization of the reactants through combined covalent and coordinative bonds (dative OTi interactions). Even reactions with the difficult, monodentate, C 2v ‐symmetric maleimide dienophiles give the desired adducts in high yields and respectable enantioselectivities [Eq. (a)]. R 1 = H, CH 3 ; R 2 = CH 3 , PhCH 2 , p ‐BrC 6 H 4 CH 2 , ( R )‐PhCH 2 (CH 3 ).