Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 1, Pages 420-424Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja511247z
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Funding
- MEXT (Japan) of Hokkaido University
- JSPS
- Grants-in-Aid for Scientific Research [14J02341, 26620053] Funding Source: KAKEN
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The first catalytic enantioselective nucleophilic borylation of a C-O double bond has been achieved. A series of aldehydes reacted with a diboron reagent in the presence of a copper(I)/DTBM-SEGPHOS complex catalyst using MeOH as a proton source to give the corresponding optically active a-alkoxyorganoboronate esters with excellent enantioselectivities. Furthermore, the products could be readily converted to the corresponding functionalized chiral alcohol derivatives through stereospecific C-C bond forming reactions involving the stereogenic C-B bond.
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