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- Title
Ring Expansion of Epoxides under Brønsted Base Catalysis: Formal [3+2] Cycloaddition of β,γ-Epoxy Esters with Imines Providing 2,4,5-Trisubstituted 1,3-Oxazolidines.
- Authors
Kondoh, Azusa; Odaira, Kenta; Terada, Masahiro
- Abstract
A novel ring-expansion reaction of epoxides under Brønsted base catalysis was developed. The formal [3+2] cycloaddition reaction of β,γ-epoxy esters with imines proceeds in the presence of triazabicyclodecene (TBD) as a superior Brønsted 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 Brønsted base catalyst to generate α,β-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.
- Subjects
RING formation (Chemistry); EPOXY compounds; BRONSTED acids; IMINES; OXAZOLIDINES; BICYCLODECENES; LEWIS acids
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 38, p11392
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201505893