Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 41, Pages 14620-14624Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201908299
Keywords
allylation; asymmetric catalysis; double-bond transposition; homoallylic compounds; palladium
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Funding
- MEXT [15H05756]
- Grants-in-Aid for Scientific Research [15H05756] Funding Source: KAKEN
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We report the highly diastereo- and enantioselective preparation of (E)-delta-boryl-substituted anti-homoallylic alcohols in two steps from terminal alkynes. This method consists of a cobalt(II)-catalyzed 1,1-diboration reaction of terminal alkynes with B(2)pin(2) and a palladium(I)-mediated asymmetric allylation reaction of the resulting 1,1-di(boryl)alk-1-enes with aldehydes in the presence of a chiral phosphoric acid. Propyne, which is produced as the byproduct during petroleum refining, could be used as the starting material to construct homoallylic alcohols that are otherwise difficult to synthesize with high stereocontrol.
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