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Diastereoselective Epoxidation of Allylic Diols Derived from Baylis-Hillman Adducts

Ricardo S. Porto, Mario L. A. A. Vasconcellos, Elizete Ventura, Fernando Coelho*

*Laboratory of Synthesis of Natural Products and Drugs, Organic Chemistry Department, Chemistry Institute/Unicamp, PO Box 6154, 13084-971 Campinas SP, Brazil, Email:

R. S. Porto, M. L. A. A. Vasconcellos, E. Ventura, F. Coelho, Synthesis, 2005, 2297-2306.

DOI: 10.1055/s-2005-872091


The results of a highly diastereoselective epoxidation of allylic diols derived from Baylis-Hillman adducts are reported. The formation of an intramolecular hydrogen bond seems to be responsible for the high anti diastereoselection obtained in this epoxidation reaction. The results are complementary to those obtained in the direct epoxidation of Baylis-Hillman adducts, in which an elevated syn diastereoselectivity was observed.

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Key Words

Baylis-Hillman reaction, epoxidation, allylic alcohol, silicon, diastereoselectivity, DIBAL-H, MCPBA, TBDMS ethers

ID: J66-Y2005-1530