Org Lett. 2007 Apr 26;9(9):1623-6. Epub 2007 Apr 5.

Preparation of 2-trialkylsiloxy- substituted 1,3-dienes and their diels-alder/cross-coupling reactions.

Pidaparthi RR, Welker ME, Day CS, Wright MW.

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Department of Chemistry, Wake Forest University, P.O. Box 7486, Winston-Salem, North Carolina 27109, USA.

Abstract

[reaction: see text] 2-Triethylsiloxy-substituted 1,3-butadiene has been prepared in gram quantities from chloroprene via a simple synthetic procedure. Silatrane and catechol-substituted analogues of this main group element substituted diene were prepared by ligand exchange and characterized by X-ray crystallography in addition to standard spectroscopic techniques. Diels-Alder reactions of these dienes are reported as well as subsequent TBAF assisted/Pd-catalyzed Hiyama cross-coupling reactions of those Diels-Alder adducts.

PMID:: 17408275; [PubMed]

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Preparation of 2-trialkylsiloxy- substituted 1,3-dienes and their diels-alder/cross-coupling reactions.

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