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
This publication has 43 references indexed in Scilit:
- One-Carbon Chain Extension of Esters to α-Chloroketones: A Safer Route without DiazomethaneThe Journal of Organic Chemistry, 2004
- Syntheses of FDA Approved HIV Protease InhibitorsSynthesis, 2001
- A Mechanistic Investigation of Alkene Epoxidation by Sterically Encumbered trans-Dioxoruthenium(VI) PorphyrinsThe Journal of Organic Chemistry, 1999
- Direct Oxidative Deprotection of Trimethylsilyl Ethers to their Corresponding Carbonyl Compounds with Bis (trimethylsilyl) Chromate Supported onto Silica Gel in Aprotic SolventSynthetic Communications, 1999
- Deprotection and Direct Oxidative Deprotection of Trimethylsilyl Ethers to their Corresponding Alcohols and Carbonyl Compounds with Tris[trinitratocerium(IV)] Paraperiodate, [(NO3)3Ce]3.H2IO6, in an Aprotic SolventSynthetic Communications, 1996
- Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavageChemical Reviews, 1992
- Shape-selective olefin epoxidation catalyzed by manganese picnic basket porphyrinsJournal of the American Chemical Society, 1990
- Membrane-spanning steroidal metalloporphyrins as site-selective catalysts in synthetic vesiclesJournal of the American Chemical Society, 1987
- Epoxidation of olefins by cytochrome P-450 model compounds: kinetics and stereochemistry of oxygen atom transfer and origin of shape selectivityJournal of the American Chemical Society, 1985
- Stereospecific, regioselective, and catalytic monoepoxidation of polyolefins by the use of a P-450 model, dihydrogen-dioxygen-TPP.cntdot.Mn-colloidal platinumJournal of the American Chemical Society, 1984