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