期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 38, 页码 11240-11244出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201505893
关键词
asymmetric synthesis; bronsted base; cycloaddition; organocatalyst; ring expansion
资金
- Innovative Areas Advanced Molecular Transformations by Organocatalysts from MEXT (Japan)
- JSPS
- Grants-in-Aid for Scientific Research [25810057] Funding Source: KAKEN
A novel ring-expansion reaction of epoxides under Bronsted base catalysis was developed. The formal [3+2] cycloaddition reaction of beta,gamma-epoxy esters with imines proceeds in the presence of triazabicyclodecene (TBD) as a superior Bronsted base catalyst to afford 2,4,5-trisubstituted 1,3-oxazolidines in a highly diastereoselective manner. This reaction involves the ring opening of the epoxides with the aid of the Bronsted base catalyst to generate alpha,beta-unsaturated esters having an alkoxide at the allylic position, which would formally serve as a synthetic equivalent of the 1,3-dipole, followed by a cycloaddition reaction with imines in a stepwise fashion. This methodology enables the facile synthesis of enantioenriched 1,3-oxazolidines from easily accessible enantioenriched epoxides.
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