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Home   •   Spotlight  •  rlist1q04j  •  Most Requested Journal Articles 1Q04-Chemistry and Related (7)
Most Requested Journal Articles 1Q04-Chemistry and Related
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Following is one of the journal articles most requested by researchers using CAS online services.



CAS indexed 108 chemical substances from this document.
CAS subject entries for this document include: Metathesis; Metathesis catalysts; Stereoselective synthesis; and 1 additional concept.

CAPLUS COPYRIGHT 2004 ACS on STN

TITLE: A General Model for Selectivity in Olefin Cross Metathesis
AUTHOR(S): Chatterjee, Arnab K.; Choi, Tae-Lim; Sanders, Daniel P.; Grubbs, Robert H.
CORPORATE SOURCE: Arnold and Mabel Beckman Laboratories for Chemical Synthesis Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA, 91125, USA
SOURCE: Journal of the American Chemical Society (2003), 125(37), 11360-11370 CODEN: JACSAT; ISSN: 0002-7863
PUBLISHER: American Chemical Society
LANGUAGE: English
ABSTRACT:
In recent years, olefin cross metathesis (CM) has emerged as a powerful and convenient synthetic technique in org. chem.; 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 alcs., tertiary allylic alcs., 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 intermol. cross metathesis reactions.

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Updated 5/4/2007 7:25:10 AM
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