Preparation and exo-selective [4+2] cycloaddition reactions of cobaloxime-substituted 1,3-dienes

Welker, Mark E.; Wright, Marcus W.; Stokes, Heather L.; Richardson, Belinda; Adams, Torrey A.; Smalley, Terrence L.; Vaughn, Stacia P.; Lohr, G. J.; Liable‐Sands, Louise M.; Rheingold, Arnold L.

doi:10.1016/s1052-2077(97)80007-8

Cited by 13 publications

(1 citation statement)

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“…We have been interested in the preparation and reaction chemistry of metal-substituted dienes for over 20 years. Initially, we prepared a number of transition metal-substituted dienes [1,2] for these studies but, more recently, we have been interested in the investigation of silicon- and boron-substituted dienes [3,4,5,6,7]. We have reported the preparation of 2-silicon-substituted 1,3-butadienes by a variety of synthetic routes and demonstrated that they could be used in sequential Diels-Alder/cross-coupling reactions [8,9,10,11,12,13].…”

Section: Introductionmentioning

confidence: 99%

Preparation and Reaction Chemistry of Novel Silicon-Substituted 1,3-Dienes

Choudhury

Welker

2015

Molecules

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2-Silicon-substituted 1,3-dienes containing non transferrable groups known to promote transmetallation were prepared by Grignard chemistry and enyne metathesis. These dienes participated in one pot metathesis/Diels-Alder reactions in regio-and diastereoselective fashions. Electron-rich alkenes showed the fastest rates in metathesis reactions, and ethylene, a commonly used metathesis promoter slowed enyne metathesis. 2-Pyridyldimethylsilyl and 2-thienyldimethylsilyl substituted Diels-Alder cycloadducts participated in cross-coupling chemistry and the 2-thienyldimethylsilyl substituted cycloadducts underwent cross-coupling under very mild reaction conditions.

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