Item Details

abstract

An ene-yne cross metathesis of silyl substituted alkynes and alkenes followed by a Diels-Alder reaction of the metathesis product 2-silyl-1,3-dienes has been developed. The dienes thus prepared in situ were shown to participate in highly diastereoselective Diels-Alder reactions. In one case the silicon substituted Diels-Alder cycloadduct was subsequently used without isolation and purification in a Hiyama cross coupling reaction. The cross coupling reactions enable these silicon dienes to be used as synthons for a variety of other dienes.

National Science Foundation CHE-0749759 (sponsorship)

subject

multicomponent reactions

contributor

Junker, Christopher S. (author)

Welker, Mark E. (author)

date

2012-05-17T16:30:21Z (accessioned)

2012-05-17T16:30:21Z (available)

2012 (issued)

identifier

NOTICE: this is the author’s version of a work that was accepted for publication in . Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. (citation)

Junker CS, Welker ME, Ruthenium Carbenes as Catalysts in stereoselective ene-yne Metathesis/Diels-Alder and ene-yne Metathesis/Diels-Alder/Cross coupling multicomponent reactions, Tetrahedron (2012), doi: 10.1016/j.tet.2012.05.011 (citation)

http://hdl.handle.net/10339/37157 (uri)

http://dx.doi.org/10.1016/j.tet.2012.05.011 (uri)

language

en_US (iso)

source

Tetrahedron

title

Ruthenium Carbenes as Catalysts in stereoselective ene-yne Metathesis/Diels-Alder and ene-yne Metathesis/Diels-Alder/Cross coupling multicomponent reactions

type

Article