Metalloporphyrin-Catalyzed Diastereoselective Epoxidation of Allyl-Substituted Alkenes
- 21 April 2005
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (11) , 4226-4232
- https://doi.org/10.1021/jo047733c
Abstract
By using [Mn(2,6-Cl2TPP)Cl] (1) as a catalyst and Oxone/H2O2 as an oxidant, we have developed an efficient method for erythro-selective epoxidation of acyclic allyl-substituted alkenes, including allylic alcohols, amines, and esters. Up to 9:1 erythro selectivities for terminal allyllic alkenes could be achieved, which are significantly higher than that achieved using m-CPBA as an oxidant. In addition, the synthetic utilities of this epoxidation method were highlighted in stereoselective synthesis of key anti-HIV drug intermediates and epoxidation of glycals.Keywords
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