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. 2002 Apr 19;67(8):2435-46.
doi: 10.1021/jo010838k.

Designing new chiral ketone catalysts. Asymmetric epoxidation of cis-olefins and terminal olefins

Hongqi Tian  1 , Xuegong She, Hongwu Yu, Lianhe Shu, Yian Shi
Affiliations

Designing new chiral ketone catalysts. Asymmetric epoxidation of cis-olefins and terminal olefins

Hongqi Tian et al. J Org Chem. .

Abstract

This paper describes a new class of chiral oxazolidinone ketone catalyst for asymmetric epoxidation. High ee values have been obtained for a number of cyclic and acyclic cis-olefins. The epoxidation was stereospecific with no isomerization observed in the epoxidation of acyclic systems. Encouragingly high ee values have also been obtained for a number of terminal olefins. Mechanistic studies show that electronic interactions play an important role in stereodifferentiation.

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