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Chiral Brønsted Acids in the Catalytic Asymmetric Nazarov Cyclization—The First Enantioselective Organocatalytic Electrocyclic Reaction
Author(s) -
Rueping Magnus,
Ieawsuwan Winai,
Antonchick Andrey P.,
Nachtsheim Boris J.
Publication year - 2007
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.200604809
Subject(s) - enantioselective synthesis , catalysis , brønsted–lowry acid–base theory , diastereomer , chemistry , organocatalysis , combinatorial chemistry , organic chemistry , stereochemistry
Low catalyst loadings , high enantioselectivities, mild conditions, and fast reaction times are the important features of the first enantioselective organocatalytic electrocyclic reaction: a Nazarov cyclization leading to the synthesis of substituted five‐membered rings with a chiral Brønsted acid as a catalyst (see scheme). A further advantage of this method is the possible entry to all four diastereomers of the product.