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 |
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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