Abstract
By using [Mn(2,6-Cl2TPP)Cl] (1) as a catalyst and Oxone/H 2O2 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.
Original language | English |
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Pages (from-to) | 4226-4232 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 70 |
Issue number | 11 |
DOIs | |
Publication status | Published - 27 May 2005 |
Externally published | Yes |
ASJC Scopus subject areas
- Organic Chemistry