Details
| Original language | English |
|---|---|
| Pages (from-to) | 717-723 |
| Number of pages | 7 |
| Journal | Journal of Organic Chemistry |
| Volume | 56 |
| Issue number | 2 |
| Publication status | Published - 1 Jan 1991 |
| Externally published | Yes |
Abstract
Ring-opening of epoxides 1 by heteroatom-substituted allylanions 2 occurs with high regioselectivity. In situ tosylation of the resulting alkoxides 3 or tosylation of the corresponding alcohols 4 yields 4-pentenyl tosylates 5. Anion generation by deprotonation or desilylation gives vinylcyclopropanes 9 by an SNi process. The approach allows annulation of vinylcyclopropanes onto existing five- and six-membered rings and synthesis of vinyl-cyclopropanes with functionality on the olefin.
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
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In: Journal of Organic Chemistry, Vol. 56, No. 2, 01.01.1991, p. 717-723.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Synthesis of Vinylcyclopropanes from Epoxides
AU - Schaumann, Ernst
AU - Kirschning, Andreas
AU - Narjes, Frank
PY - 1991/1/1
Y1 - 1991/1/1
N2 - Ring-opening of epoxides 1 by heteroatom-substituted allylanions 2 occurs with high regioselectivity. In situ tosylation of the resulting alkoxides 3 or tosylation of the corresponding alcohols 4 yields 4-pentenyl tosylates 5. Anion generation by deprotonation or desilylation gives vinylcyclopropanes 9 by an SNi process. The approach allows annulation of vinylcyclopropanes onto existing five- and six-membered rings and synthesis of vinyl-cyclopropanes with functionality on the olefin.
AB - Ring-opening of epoxides 1 by heteroatom-substituted allylanions 2 occurs with high regioselectivity. In situ tosylation of the resulting alkoxides 3 or tosylation of the corresponding alcohols 4 yields 4-pentenyl tosylates 5. Anion generation by deprotonation or desilylation gives vinylcyclopropanes 9 by an SNi process. The approach allows annulation of vinylcyclopropanes onto existing five- and six-membered rings and synthesis of vinyl-cyclopropanes with functionality on the olefin.
UR - http://www.scopus.com/inward/record.url?scp=0003245764&partnerID=8YFLogxK
U2 - 10.1021/jo00002a043
DO - 10.1021/jo00002a043
M3 - Article
AN - SCOPUS:0003245764
VL - 56
SP - 717
EP - 723
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 2
ER -