Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 24, Pages 6989-6993Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201702611
Keywords
allylation; asymmetric synthesis; homoallylic compounds; organocatalysis; palladium
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Funding
- MEXT [15H05756, 16K05694]
- Grants-in-Aid for Scientific Research [15H05756, 16K05694] Funding Source: KAKEN
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(E)-delta-Boryl-substituted anti-homoallylic alcohols are synthesized in a highly diastereo- and enantioselective manner from 1,1-di(boryl) alk-3-enes and aldehydes. Mechanistically, the reaction consists of 1) palladium-catalyzed double-bond transposition of the 1,1-di(boryl) alk-3-enes to 1,1-di(boryl) alk-2-enes, 2) chiral phosphoric acid catalyzed allylation of aldehydes, and 3) palladium-catalyzed geometrical isomerization from the Z to Eisomer. As a result, the configurations of two chiral centers and one double bond are all controlled with high selectivity in a single reaction vessel.
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