Abstract
Several alkylidenesilacyclopropanes were prepared by silver-mediated silylene transfer to allenes. Oxasilacyclopentanes derived from allenes were prepared with high regio- and diastereoselectivity by a two-step, one-flask silacyclopropanation/carbonyl insertion reaction. Triols and homoallylic alcohols were formed diastereoselectively by functionalizing the oxasilacyclopentanes. An optically active allene (>98% ee) was utilized to synthesize an enantiopure homoallylic alcohol in 96% ee.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 2173-2175 |
| Number of pages | 3 |
| Journal | Organic Letters |
| Volume | 11 |
| Issue number | 10 |
| DOIs | |
| State | Published - May 21 2009 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Buchner, K. M., Clark, T. B., Loy, J. M. N., Nguyen, T. X., & Woerpel, K. A. (2009). Alkylidenesilacyclopropanes derived from allenes: Applications to the selective synthesis of triols and homoallylic alcohols. Organic Letters, 11(10), 2173-2175. https://doi.org/10.1021/ol900456v