Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 31, Pages 10903-10908Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b06408
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Funding
- MEXT [JP15H05756, JP16K05694]
- ACT-C Program from JST [JPMJCR12Z9]
- JSPS
- Kyoto University Foundation
- Grants-in-Aid for Scientific Research [15H05756, 16K05694] Funding Source: KAKEN
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A cationic ruthenium(II) complex catalyzes double-bond transposition of 1,1-di(boryl)alk-3-enes to generate in situ 1,1-di(boryl)alk-2-enes, which then undergo chiral phosphoric acid catalyzed allylation of aldehydes producing homoallylic alcohols with a (Z)-vinylboronate moiety. 1,2-Anti stereochemistry is installed in an enantioselective manner. The (Z)-geometry forged in the products allows their isolation in a form of 1,2-oxaborinan-3-enes, upon which further synthetic transformations are operated.
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