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Asymmetric Heck Reaction
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.
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Citations
Cites
Synthetic Studies of Biologically Active Marine Cyclopeptides
Wipf, P. (1995) · Chemical Reviews · doi:10.1021/cr00038a013 · Cited by 574
Cited by
Cascade Reactions in Total Synthesis
Nicolaou, K. C., Edmonds, D. J., & Bulger, P. G. (2006) · Angewandte Chemie International Edition · doi:10.1002/anie.200601872 · Cited by 2,101
Phan, N. T. S., Van Der Sluys, M., & Jones, C. W. (2006) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.200505473 · Cited by 1,905
Enantioselective Heck Arylations of Acyclic Alkenyl Alcohols Using a Redox-Relay Strategy
Werner, E. W., Mei, T.-S., Burckle, A. J., & Sigman, M. S. (2012) · Science · doi:10.1126/science.1229208 · Cited by 477
Pierron, J., Malan, C., Creus, M., Gradinaru, J., Hafner, I., Ivanova, A., Sardo, A., & Ward, T. R. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200703159 · Cited by 117
Metadata
- Authors
- Shibasaki, M., Vogl, E. M., & Ohshima, T.
- Venue
- Advanced Synthesis & Catalysis
- Publisher
- Wiley
- Published
- 2004-12
- Volume
- 346
- Issue
- 13-15
- Pages
- 1533-1552
- ISSN
- 1615-4150 (ISSN-L)
- 1615-4169
- OpenAlex
- W2118779428
- Cited by
- 327
- References
- 1
- FWCI
- 9.11
- Type
- journal article
- Language
- en
- Open access
- closed
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