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: teckpeng
ntu.edu.sg
F. Liu, T.-P. Loh, Org. Lett., 2007, 9, 2063-2066.
DOI: 10.1021/ol070506n
Abstract
An efficient method allows the construction of 2,6-cis-4,5-dibromo-tetrasubstituted tetrahydropyran rings with well-controlled stereochemistry in good yields.
see article for more examples
proposed mechanism
Key Words
Tetrahydropyrans, Prins Reaction, 1,2-Dibromoalkanes
ID: J54-Y2007-1620
