Tuning of vinylborane dienophilicity. Optimization of reactivity, regioselectivity, endo-stereoselectivity, and reagent stability

DA Singleton, JP Martinez, JV Watson, GM Ndip

Index: Singleton, Daniel A.; Martinez, Jose P.; Watson, Jose V.; Ndip, Grace M. Tetrahedron, 1992 , vol. 48, # 28 p. 5831 - 5838

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Citation Number: 45

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 25° C. Surprisingly, trivinylborane is the most reactive, and reacts about 18 times faster than the vinyldialkylboranes with cyclopentadiene. Vinyl-9-BBN is the most regioselective ...