A method for the synthesis of alpha-chiral allylboronates featuring the Cu(I)-catalyzed enantioselective substitution of readily available allylic carbonates with a diboron is described. Using this method, various alpha-chiral allylboronates, including functionalized allylboronates, were successfully synthesized, with high enantiomeric purity.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ja076634o | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
An efficient approach to chiral allyloxyamines by stereospecific allylation of nitrosoarenes with chiral allylboronates.
Angew Chem Int Ed Engl
March 2015
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstrasse 40, 48149 Münster (Germany).
A novel and efficient approach to allyloxyamines by the allylation of nitrosoarenes with α-chiral allylboronates is described. C-O bond formation occurs with high stereospecificity and the product allyloxyamines are easily transformed into valuable chiral building blocks such as isoxazolidines and allylic alcohols. The reaction features complete regioselectivity (O-selectivity), high E/Z selectivity, and excellent chirality transfer.
View Article and Find Full Text PDFDirect enantio-convergent transformation of racemic substrates without racemization or symmetrization.
Nat Chem
November 2010
Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan.
Asymmetric reactions that transform racemic mixtures into enantio-enriched products are in high demand, but classical kinetic resolution produces enantiopure compounds in <50% yield even in an ideal case. Many deracemization processes have thus been developed including dynamic kinetic resolution and dynamic kinetic asymmetric transformation, which can provide enantio-enriched products even after complete conversion of the racemic starting materials. However, these dynamic processes require racemization or symmetrization of the substrates or intermediates.
View Article and Find Full Text PDFCopper-catalyzed enantioselective substitution of allylic carbonates with diboron: an efficient route to optically active alpha-chiral allylboronates.
J Am Chem Soc
December 2007
Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan.
A method for the synthesis of alpha-chiral allylboronates featuring the Cu(I)-catalyzed enantioselective substitution of readily available allylic carbonates with a diboron is described. Using this method, various alpha-chiral allylboronates, including functionalized allylboronates, were successfully synthesized, with high enantiomeric purity.
View Article and Find Full Text PDFCatalytic enantioselective three-component hetero-[4+2] cycloaddition/allylboration approach to alpha-hydroxyalkyl pyrans: scope, limitations, and mechanistic proposal.
Chemistry
April 2006
Department of Chemistry, Gunning-Lemieux Chemistry Centre, University of Alberta, Edmonton, AB T6G 2G2, Canada.
This article describes the design and optimization of a catalytic enantioselective three-component hetero-[4+2] cycloaddition/allylboration reaction between 3-boronoacrolein, enol ethers, and aldehydes to afford alpha-hydroxyalkyl dihydropyrans. The key substrate, 3-boronoacrolein pinacolate (2) was found to be an exceptionally reactive heterodiene in the hetero-[4+2] cycloaddition catalyzed by Jacobsen's chiral Cr(III) catalyst 1. The scope and limitations of this process were thoroughly examined.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!