期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 41, 页码 14620-14624出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201908299
关键词
allylation; asymmetric catalysis; double-bond transposition; homoallylic compounds; palladium
资金
- MEXT [15H05756]
- Grants-in-Aid for Scientific Research [15H05756] Funding Source: KAKEN
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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