Asymmetric Heck reaction

Masakatsu Shibasaki, Erasmus M. Vogl, Takashi Ohshima

Research output: Contribution to journalReview article

269 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1533-1552
Number of pages20
JournalAdvanced Synthesis and Catalysis
Volume346
Issue number13-15
DOIs
Publication statusPublished - Dec 1 2004

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Regioselectivity
Alkenes
Isomerization
Biological Products
Olefins
Carbon
Ligands

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

Asymmetric Heck reaction. / Shibasaki, Masakatsu; Vogl, Erasmus M.; Ohshima, Takashi.

In: Advanced Synthesis and Catalysis, Vol. 346, No. 13-15, 01.12.2004, p. 1533-1552.

Research output: Contribution to journalReview article

Shibasaki, Masakatsu ; Vogl, Erasmus M. ; Ohshima, Takashi. / Asymmetric Heck reaction. In: Advanced Synthesis and Catalysis. 2004 ; Vol. 346, No. 13-15. pp. 1533-1552.
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