Designing New Chiral Ketone Catalysts. Asymmetric Epoxidation of cis-Olefins and Terminal Olefins
- 20 March 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (8), 2435-2446
- https://doi.org/10.1021/jo010838k
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.Keywords
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