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A General Model for Selectivity in Olefin Cross Metathesis

Chatterjee, Arnab K., Choi, Tae-Lim, Sanders, Daniel P., Grubbs, Robert H.·2003·Journal of the American Chemical Society
DOI 10.1021/ja0214882
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Abstract

In recent years, olefin cross metathesis (CM) has emerged as a powerful and convenient synthetic technique in organic chemistry; however, as a general synthetic method, CM has been limited by the lack of predictability in product selectivity and stereoselectivity. Investigations into olefin cross metathesis with several classes of olefins, including substituted and functionalized styrenes, secondary allylic alcohols, tertiary allylic alcohols, and olefins with alpha-quaternary centers, have led to a general model useful for the prediction of product selectivity and stereoselectivity in cross metathesis. As a general ranking of olefin reactivity in CM, olefins can be categorized by their relative abilities to undergo homodimerization via cross metathesis and the susceptibility of their homodimers toward secondary metathesis reactions. When an olefin of high reactivity is reacted with an olefin of lower reactivity (sterically bulky, electron-deficient, etc.), selective cross metathesis can be achieved using feedstock stoichiometries as low as 1:1. By employing a metathesis catalyst with the appropriate activity, selective cross metathesis reactions can be achieved with a wide variety of electron-rich, electron-deficient, and sterically bulky olefins. Application of this model has allowed for the prediction and development of selective cross metathesis reactions, culminating in unprecedented three-component intermolecular cross metathesis reactions.

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Metadata

Authors
Chatterjee, A. K., Choi, T.-L., Sanders, D. P., & Grubbs, R. H.
Venue
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Published
2003-08-20
Volume
125
Issue
37
Pages
11360-11370
ISSN
  • 0002-7863 (ISSN-L)
  • 1520-5126
DOI
10.1021/ja0214882
OpenAlex
W2009381692
Cited by
1,550
References
0
FWCI
45.79
Type
journal article
Language
en
Open access
closed

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CoChat. (2026). Citation check: A General Model for Selectivity in Olefin Cross Metathesis. https://app.cochat.ai/papers/10.1021/ja0214882
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Chatterjee, A. K., Choi, T.-L., Sanders, D. P., & Grubbs, R. H. (2003). A General Model for Selectivity in Olefin Cross Metathesis. Journal of the American Chemical Society. https://doi.org/10.1021/ja0214882

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