Under Lewis acid activation, the new α-hydroxy-spiro epoxide scaffold 1a underwent an original tandem Payne/Meinwald rearrangement affording the cyclopentyl hydroxymethylketone 6 in a stereospecific manner, while a Meinwald-type epoxide rearrangement occurred when the derived α-trimethylsilyloxy-spiro epoxide 2a was treated with MABR, yielding stereoselectively the cyclohexane carbaldehyde 9.
|Original language||English (US)|
|Number of pages||4|
|Journal||Organic and Biomolecular Chemistry|
|State||Published - Jan 21 2012|
Bibliographical noteFunding Information:
I thank A. Kost, D. Williams, and J. Washizaki for excellent electron microscopy and photography. This work was supported by grants from the National Science Foundation and the National Institute of General Medical Sciences.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry