Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 18, Pages 7071-7074Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo060738k
Keywords
-
Categories
Ask authors/readers for more resources
A tandem addition/silyl-Prins reaction efficiently affords cis-2,6-disubstituted dihydropyrans (DHPs) using 5 mol % of BiBr3 in CH2Cl2. The reaction occurs between delta-triethyl-silyloxyvinyltrimethylsilanes and a variety of aldehydes to give good to excellent isolated yields of DHPs. The diastereoselectivities in the crude products are significantly affected by aldehyde substitution with electron-rich aldehydes, providing 2-3: 1 (cis: trans) and neutral (or electron-poor) aldehydes affording dr >= 19: 1 (cis: trans).
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available