Intercepting the Breslow Intermediate via Claisen Rearrangement: Synthesis of Complex Tertiary Alcohols without Organometallic Reagents

by Alwarsh, Sefat; Ayinuola, Kolawole; Dormi, Silvana S.; McIntosh, Matthias C.

A novel Claisen rearrangement in which the Breslow intermediate is engaged as a hydroxy-substituted N,S-ketene acetal to provide complex 3 degrees alcohols without the use of organometallic reagents is reported. The reaction constitutes an unprecedented reactivity mode for the Breslow intermediate.

Journal
Organic Letters
Volume
15
Issue
1
Year
2013
Start Page
3-5
URL
https://dx.doi.org/10.1021/ol303053c
ISBN/ISSN
1523-7052; 1523-7060
DOI
10.1021/ol303053c