Catalytic asymmetric transformations of racemic α-borylmethyl-(E)-crotylboronate via kinetic resolution or enantioconvergent reaction pathways

We report herein catalytic asymmetric transformations of racemic α-borylmethyl-(E)-crotylboronate. The Brønsted acid-catalyzed kinetic resolution–allylboration reaction sequence of the racemic reagent gave (Z)-δ-hydroxymethyl-anti-homoallylic alcohols with high Z-selectivities and enantioselectiviti...

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Autores principales: Gao, Shang, Liu, Jiaming, Chen, Ming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8528009/
https://www.ncbi.nlm.nih.gov/pubmed/34777758
http://dx.doi.org/10.1039/d1sc04047b
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author Gao, Shang
Liu, Jiaming
Chen, Ming
author_facet Gao, Shang
Liu, Jiaming
Chen, Ming
author_sort Gao, Shang
collection PubMed
description We report herein catalytic asymmetric transformations of racemic α-borylmethyl-(E)-crotylboronate. The Brønsted acid-catalyzed kinetic resolution–allylboration reaction sequence of the racemic reagent gave (Z)-δ-hydroxymethyl-anti-homoallylic alcohols with high Z-selectivities and enantioselectivities upon oxidative workup. In parallel, enantioconvergent pathways were utilized to synthesize chiral nonracemic 1,5-diols and α,β-unsaturated aldehydes with excellent optical purity.
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spelling pubmed-85280092021-11-12 Catalytic asymmetric transformations of racemic α-borylmethyl-(E)-crotylboronate via kinetic resolution or enantioconvergent reaction pathways Gao, Shang Liu, Jiaming Chen, Ming Chem Sci Chemistry We report herein catalytic asymmetric transformations of racemic α-borylmethyl-(E)-crotylboronate. The Brønsted acid-catalyzed kinetic resolution–allylboration reaction sequence of the racemic reagent gave (Z)-δ-hydroxymethyl-anti-homoallylic alcohols with high Z-selectivities and enantioselectivities upon oxidative workup. In parallel, enantioconvergent pathways were utilized to synthesize chiral nonracemic 1,5-diols and α,β-unsaturated aldehydes with excellent optical purity. The Royal Society of Chemistry 2021-09-20 /pmc/articles/PMC8528009/ /pubmed/34777758 http://dx.doi.org/10.1039/d1sc04047b Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Gao, Shang
Liu, Jiaming
Chen, Ming
Catalytic asymmetric transformations of racemic α-borylmethyl-(E)-crotylboronate via kinetic resolution or enantioconvergent reaction pathways
title Catalytic asymmetric transformations of racemic α-borylmethyl-(E)-crotylboronate via kinetic resolution or enantioconvergent reaction pathways
title_full Catalytic asymmetric transformations of racemic α-borylmethyl-(E)-crotylboronate via kinetic resolution or enantioconvergent reaction pathways
title_fullStr Catalytic asymmetric transformations of racemic α-borylmethyl-(E)-crotylboronate via kinetic resolution or enantioconvergent reaction pathways
title_full_unstemmed Catalytic asymmetric transformations of racemic α-borylmethyl-(E)-crotylboronate via kinetic resolution or enantioconvergent reaction pathways
title_short Catalytic asymmetric transformations of racemic α-borylmethyl-(E)-crotylboronate via kinetic resolution or enantioconvergent reaction pathways
title_sort catalytic asymmetric transformations of racemic α-borylmethyl-(e)-crotylboronate via kinetic resolution or enantioconvergent reaction pathways
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8528009/
https://www.ncbi.nlm.nih.gov/pubmed/34777758
http://dx.doi.org/10.1039/d1sc04047b
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AT liujiaming catalyticasymmetrictransformationsofracemicaborylmethylecrotylboronateviakineticresolutionorenantioconvergentreactionpathways
AT chenming catalyticasymmetrictransformationsofracemicaborylmethylecrotylboronateviakineticresolutionorenantioconvergentreactionpathways

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