Development of α-Borylmethyl-(<i>Z</i>)-crotylboronate Reagent and Enantioselective Syntheses of (<i>E</i>)-δ-Hydroxymethyl-<i>syn</i>-homoallylic Alcohols via Highly Stereoselective Allylboration
Jiaming Liu, Shang Gao, Ming Chen
Abstract
We report herein the development of α-borylmethyl-(Z)-crotylboronate reagent and the application in highly stereo- and enantioselective syntheses of (E)-δ-hydroxymethyl-syn-homoallylic alcohols. Starting from 1,4-pentadiene, α-borylmethyl-(Z)-crotylboronate was synthesized in two steps with high Z-selectivity and enantioselectivity. Subsequent aldehyde allylboration with the developed boron reagent gave highly enantioenriched (E)-δ-hydroxymethyl-syn-homoallylic alcohols upon oxidative workup.
Topics & Concepts
Enantioselective synthesisHydroxymethylChemistryReagentStereoselectivityAldehydeSelectivityOrganic chemistryCombinatorial chemistryCatalysisOrganoboron and organosilicon chemistryAsymmetric Synthesis and CatalysisAdvanced Synthetic Organic Chemistry