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Asymmetric Heck Reaction
Author(s) -
Shibasaki Masakatsu,
Vogl Erasmus M.,
Ohshima Takashi
Publication year - 2004
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200404203
Subject(s) - chemistry , enantioselective synthesis , heck reaction , regioselectivity , isomerization , quaternary carbon , alkene , enantiomer , organic chemistry , combinatorial chemistry , palladium , catalysis
The asymmetric Heck reaction is a powerful method for the synthesis of both tertiary and quaternary chiral carbon centers, with an enantiomeric excess often greater than 80%, and in some cases much higher (up to 99% ee). A variety of carbocyclic and heterocyclic systems can be constructed, including spirocyclic systems. The scope of the reaction with respect to the product alkene isomerization is somewhat limited by problems of regioselectivity, however, these problems are surmountable, and a new generation of ligands that dissociate more rapidly from the products, might improve both enantio‐ and regiocontrol. A variety of chiral compounds prepared by the asymmetric Heck reaction were successfully utilized in the enantioselective syntheses of complex natural products.