Abstract
TiF4 has proven to be the Lewis acid of choice for promoting the biomimetic addition of 2-trimethylsilylmethyl-1,5-dienes to aliphatic aldehydes with concomitant cyclization. 1,3-cis-Disubstituted methylenecyclohexanes are thus produced in good yields and high diastereoselectivity. The reaction appears to proceed via a highly concerted mechanism involving a chair-like transition state.
| Original language | English |
|---|---|
| Pages (from-to) | 5803-5806 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 46 |
| Issue number | 35 |
| DOIs | |
| Publication status | Published - Aug 29 2005 |
Keywords
- Aldehydes
- Allylsilane
- Biomimetic reactions
- Cyclization
- TiF
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
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Anastasia, L., Giannini, E., Zanoni, G., & Vidari, G. (2005). TiF4-mediated biomimetic alkylation-cyclization cascade reaction of 2-trimethylsilylmethyl-1,5-dienes with aldehydes. Tetrahedron Letters, 46(35), 5803-5806. https://doi.org/10.1016/j.tetlet.2005.06.149