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Catalytic Desymmetrizing Intramolecular Heck Reaction: Evidence for an Unusual Hydroxy‐Directed Migratory Insertion
Author(s) -
Oestreich Martin,
SempereCuller Fernando,
Machotta Axel B.
Publication year - 2004
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.200460921
Subject(s) - desymmetrization , heck reaction , intramolecular force , catalysis , chemistry , alkene , cationic polymerization , enantioselective synthesis , combinatorial chemistry , palladium , stereochemistry , medicinal chemistry , organic chemistry
Mild cationic reaction conditions are used for the efficient desymmetrization of prochiral bishomoallylic alcohols in an intramolecular Heck reaction. This is the first example of a group‐selective Heck cyclization in which the enantiotopic alkene moieties are not incorporated into a cyclic and, therefore, rigid system (see scheme). The high enantioselectivity is attributed to the hydroxy group functioning as a catalyst‐directing group, which could be a novel feature in asymmetric Heck chemistry.