Metalloporphyrin-catalyzed diastereoselective epoxidation of allyl-substituted alkenes.
By using [Mn(2,6-Cl(2)TPP)Cl] (1) as a catalyst and Oxone/H(2)O(2) 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.
Chan
Wing-Kei
WK
Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong, China.
Wong
Man-Kin
MK
Che
Chi-Ming
CM
D000475:Alkenes / Q000737:chemistry; D019380:Anti-HIV Agents / Q000737:chemistry; D002384:Catalysis; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D008345:Manganese / Q000737:chemistry*; D008665:Metalloporphyrins / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D016877:Oxidants / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000475:Alkenes; D019380:Anti-HIV Agents; D004852:Epoxy Compounds; D008665:Metalloporphyrins; D009942:Organometallic Compounds; D016877:Oxidants; D008345:Manganese