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Highly Stereoselective Prins Cyclization of (Z)- and (E)-γ-Brominated Homoallylic Alcohols to 2,4,5,6-Tetrasubstituted Tetrahydropyrans

Feng Liu and Teck-Peng Loh*

*Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637616, Email: teckpengntu.edu.sg

F. Liu, T.-P. Loh, Org. Lett., 2007, 9, 2063-2066.

DOI: 10.1021/ol070506n (free Supporting Information)


Abstract

An efficient method allows the construction of  2,6-cis-4,5-dibromo-tetrasubstituted tetrahydropyran rings with well-controlled stereochemistry in good yields.


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proposed mechanism



Key Words

Tetrahydropyrans, Prins Reaction, 1,2-Dibromoalkanes


ID: J54-Y2007-1620