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: coelho
iqm.unicamp.br
R. S. Porto, M. L. A. A. Vasconcellos, E. Ventura, F. Coelho, Synthesis, 2005, 2297-2306.
DOI: 10.1055/s-2005-872091
Abstract
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
