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Mechanistic studies on the Heck-Mizoroki cross-coupling reaction of a hindered vinylboronate ester as a key approach to developing a highly stereoselective synthesis of a Cl-C7 Z,Z,E-triene synthon for viridenomycin

Batsanov, A.S.; Knowles, J.P.; Whiting, A.

Authors

A.S. Batsanov

J.P. Knowles



Abstract

Mechanistic studies of the Heck-Mizoroki reaction of a vinylboronate ester with electronically different (four-substituted) aryl iodides shows that electron donors accelerate the cross-coupling, demonstrating that the oxidative addition step is not rate determining and that there is development of some degree of positive charge in the rate determining step. These results were used as a basis to allow the development of reaction conditions for the Heck-Mizoroki coupling of a hindered vinylboronate ester with electron deficient methyl cis-2-iodoacrylate. The resulting dienylboronate ester was converted through a series of highly stereoselective iodo-deboronations and Heck-Mizoroki reactions into a trienyl iodide precursor for further application in the total synthesis of viridenomycin.

Citation

Batsanov, A., Knowles, J., & Whiting, A. (2007). Mechanistic studies on the Heck-Mizoroki cross-coupling reaction of a hindered vinylboronate ester as a key approach to developing a highly stereoselective synthesis of a Cl-C7 Z,Z,E-triene synthon for viridenomycin. Journal of Organic Chemistry, 72(7), 2525-2532. https://doi.org/10.1021/jo0626010

Journal Article Type Article
Publication Date Mar 1, 2007
Deposit Date Sep 21, 2007
Journal Journal of Organic Chemistry
Print ISSN 0022-3263
Electronic ISSN 1520-6904
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 72
Issue 7
Pages 2525-2532
DOI https://doi.org/10.1021/jo0626010


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