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

Angewandte Chemie
Azusa KondohMasahiro Terada

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.

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Citations

Oct 7, 2016·The Journal of Organic Chemistry·Vanaparthi SatheeshTharmalingam Punniyamurthy
Jan 26, 2016·Chemistry : a European Journal·Karl Anker JørgensenKarl Anker Jørgensen
Oct 4, 2018·Chemical Communications : Chem Comm·Vanaparthi SatheeshTharmalingam Punniyamurthy
Aug 10, 2018·Chemistry : a European Journal·David Reyes Loya, Michaël De Paolis
Dec 10, 2020·Organic & Biomolecular Chemistry·Shuang YangZhenhua Ding

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