Author:
Clark-Lewis JW,McGarry EJ
Abstract
Hydroboration of
flav-3-enes has been found to be sensitive to electron release from
substituents in the A-ring. Flav-3-enes which lack electron-releasing
substituents in the A-ring give 2,4-trans-flavan-4- ols as the principal non-phenolic
products. Electron-releasing substituents in the A-ring favour boration at the
3-position, and the boranes so formed suffer ring fission, which leads to the
isolation of phenolic 1,3-diarylpropane derivatives as well as
2,3-trans-flavan-3- ols. Ring fission of the intermediate borane is minimized
by reducing the temperature of hydroboration. N.m.r. data are presented on the
compounds obtained.
Cited by
16 articles.
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