Stereoselective Syntheses of (E)-γ′,δ-Bisboryl-Substituted syn-Homoallylic Alcohols via Chemoselective Aldehyde Allylboration
M Wang, S Gao, M Chen - Organic letters, 2019 - ACS Publications
M Wang, S Gao, M Chen
Organic letters, 2019•ACS PublicationsThe development of a novel (Z)-α, δ-bisboryl-substituted crotylboron reagent is reported. Ni-
catalyzed 1, 4-diboration of dienylboronate provided the targeted crotylboronate in good
yield with high regio-and stereoselectivity. Chemo-and stereoselective addition of this
crotylboron reagent to aldehydes followed by protection of the resulting secondary hydroxyl
group gave TES-protected homoallylic alcohols bearing an alkyl and a vinyl boronate
groups with high stereoselectivities.
catalyzed 1, 4-diboration of dienylboronate provided the targeted crotylboronate in good
yield with high regio-and stereoselectivity. Chemo-and stereoselective addition of this
crotylboron reagent to aldehydes followed by protection of the resulting secondary hydroxyl
group gave TES-protected homoallylic alcohols bearing an alkyl and a vinyl boronate
groups with high stereoselectivities.
The development of a novel (Z)-α,δ-bisboryl-substituted crotylboron reagent is reported. Ni-catalyzed 1,4-diboration of dienylboronate provided the targeted crotylboronate in good yield with high regio- and stereoselectivity. Chemo- and stereoselective addition of this crotylboron reagent to aldehydes followed by protection of the resulting secondary hydroxyl group gave TES-protected homoallylic alcohols bearing an alkyl and a vinyl boronate groups with high stereoselectivities.
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