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 |
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Keywords
- Aldehydes
- Allylsilane
- Biomimetic reactions
- Cyclization
- TiF
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
TiF4-mediated biomimetic alkylation-cyclization cascade reaction of 2-trimethylsilylmethyl-1,5-dienes with aldehydes. / Anastasia, Luigi; Giannini, Elios; Zanoni, Giuseppe; Vidari, Giovanni.
In: Tetrahedron Letters, Vol. 46, No. 35, 29.08.2005, p. 5803-5806.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - TiF4-mediated biomimetic alkylation-cyclization cascade reaction of 2-trimethylsilylmethyl-1,5-dienes with aldehydes
AU - Anastasia, Luigi
AU - Giannini, Elios
AU - Zanoni, Giuseppe
AU - Vidari, Giovanni
PY - 2005/8/29
Y1 - 2005/8/29
N2 - 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.
AB - 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.
KW - Aldehydes
KW - Allylsilane
KW - Biomimetic reactions
KW - Cyclization
KW - TiF
UR - http://www.scopus.com/inward/record.url?scp=23044486560&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=23044486560&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2005.06.149
DO - 10.1016/j.tetlet.2005.06.149
M3 - Article
AN - SCOPUS:23044486560
VL - 46
SP - 5803
EP - 5806
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 35
ER -