Details
| Original language | English |
|---|---|
| Pages (from-to) | 4691-4694 |
| Number of pages | 4 |
| Journal | Tetrahedron letters |
| Volume | 32 |
| Issue number | 36 |
| Publication status | Published - 1991 |
| Externally published | Yes |
Abstract
Double Michael additions of vinylogous esters of type 1 with crotyl ester generates diastereoselectively bicyclo[2.2.2]octanone 2 with four defined chiral centers via a synclinal transition state. Thexyldimethylsilyl enol ethers of type 5 and 10 undergo smooth cyclization to bicyclo[3.3.1]nonenones 7 and bicylo[3.3.0]octenones 12 by addition of Lewis acids.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Pharmacology, Toxicology and Pharmaceutics(all)
- Drug Discovery
- Chemistry(all)
- Organic Chemistry
Cite this
- Standard
- Harvard
- Apa
- Vancouver
- BibTeX
- RIS
In: Tetrahedron letters, Vol. 32, No. 36, 1991, p. 4691-4694.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Diastereoselective double michael additions of vinylogous esters and thexyldimethylsilyl triflate-induced cyclizations
AU - Schinzer, Dieter
AU - Kalesse, Markus
PY - 1991
Y1 - 1991
N2 - Double Michael additions of vinylogous esters of type 1 with crotyl ester generates diastereoselectively bicyclo[2.2.2]octanone 2 with four defined chiral centers via a synclinal transition state. Thexyldimethylsilyl enol ethers of type 5 and 10 undergo smooth cyclization to bicyclo[3.3.1]nonenones 7 and bicylo[3.3.0]octenones 12 by addition of Lewis acids.
AB - Double Michael additions of vinylogous esters of type 1 with crotyl ester generates diastereoselectively bicyclo[2.2.2]octanone 2 with four defined chiral centers via a synclinal transition state. Thexyldimethylsilyl enol ethers of type 5 and 10 undergo smooth cyclization to bicyclo[3.3.1]nonenones 7 and bicylo[3.3.0]octenones 12 by addition of Lewis acids.
UR - http://www.scopus.com/inward/record.url?scp=0025742927&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(00)92283-4
DO - 10.1016/S0040-4039(00)92283-4
M3 - Article
AN - SCOPUS:0025742927
VL - 32
SP - 4691
EP - 4694
JO - Tetrahedron letters
JF - Tetrahedron letters
SN - 0040-4039
IS - 36
ER -