TUNING OF VINYLBORANE DIENOPHILICITY - OPTIMIZATION OF REACTIVITY, REGIOSELECTIVITY, ENDOSTEREOSELECTIVITY, AND REAGENT STABILITY Academic Article

abstract

• Simple syntheses of some vinylboranes are reported, and their properties in Diels-Alder reactions are compared. Vinyl-3,6-dimethylborepane was the most stable simple vinylborane examined, and appears to be indefinitely stable at 25C. Surprisingly, trivinylborane is the most reactive, and reacts about 18 times faster than the vinyldialkylboranes with cyclopentadiene. Vinyl-9-BBN is the most regioselective dienophile, in keeping with principally steric control of regioselectivity in Diels-Alder reactions of vinylboranes. All the dienophiles display high endo-stereoselectivity with piperylene, but vinyl-3,6-dimethylborepane displays significantly improved stereoselectivity with cyclopentadiene. In general, by choice of alkyl-substituents on boron, the reactivity, regioselectivity, endo-stereoselectivity, and stability of vinylboranes can be optimized. 1992.

authors

• Singleton, Daniel

published proceedings

• TETRAHEDRON

author list (cited authors)

• SINGLETON, D. A., MARTINEZ, J. P., WATSON, J. V., & NDIP, G. M.

citation count

• 47

complete list of authors

• SINGLETON, DA||MARTINEZ, JP||WATSON, JV||NDIP, GM

publication date

• July 1992

publisher

• Elsevier  Publisher

published in

• Tetrahedron: the international journal for the rapid publication of full original research papers and critical reviews in organic chemistr  Journal

keywords

• 34 Chemical Sciences
• 3405 Organic Chemistry
• 3407 Theoretical And Computational Chemistry

Digital Object Identifier (DOI)

• 10.1016/S0040-4020(01)90174-7

start page

• 5831

end page

• 5838

volume

• 48

issue

• 28

URL

• http%3A%2F%2Fdx.doi.org%2F10.1016%2Fs0040-4020%2801%2990174-7