Details
| Original language | English |
|---|---|
| Pages (from-to) | 8771-8774 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 36 |
| Issue number | 48 |
| Publication status | Published - 27 Nov 1995 |
| Externally published | Yes |
Abstract
The preparation and proton-induced cyclization of silyl-substituted 4,S-epoxy-l-alkanols is described The regioselectivity of intramolecular attack of the hydroxy group on the epoxy silane moiety is highly dependent on the configuration of the epoxy alcohols employed. Thus 1,4-anti epoxy alcohols exclusively yield tetrahydropyrans whereas the corresponding 1,4-syn derivates furnish a diastereomeric mixture of tetrahydrofurans.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Pharmacology, Toxicology and Pharmaceutics(all)
- Drug Discovery
- Chemistry(all)
- Organic Chemistry
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In: Tetrahedron Letters, Vol. 36, No. 48, 27.11.1995, p. 8771-8774.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Cyclizations of 5-silyl-substituted 4,5-epoxy-1-alkanols
T2 - A configuration dependent mode of ring closure
AU - Adiwidjaja, Gunadi
AU - Flörke, Holger
AU - Kirschning, Andreas
AU - Schaumann, Ernst
N1 - Funding information:: We express our gratitude to the Deutsche Forschungsgemeinschaft (grant No. Scha 231/6• I) and to the Fonds der Cbemischen Industrie for financial support.
PY - 1995/11/27
Y1 - 1995/11/27
N2 - The preparation and proton-induced cyclization of silyl-substituted 4,S-epoxy-l-alkanols is described The regioselectivity of intramolecular attack of the hydroxy group on the epoxy silane moiety is highly dependent on the configuration of the epoxy alcohols employed. Thus 1,4-anti epoxy alcohols exclusively yield tetrahydropyrans whereas the corresponding 1,4-syn derivates furnish a diastereomeric mixture of tetrahydrofurans.
AB - The preparation and proton-induced cyclization of silyl-substituted 4,S-epoxy-l-alkanols is described The regioselectivity of intramolecular attack of the hydroxy group on the epoxy silane moiety is highly dependent on the configuration of the epoxy alcohols employed. Thus 1,4-anti epoxy alcohols exclusively yield tetrahydropyrans whereas the corresponding 1,4-syn derivates furnish a diastereomeric mixture of tetrahydrofurans.
UR - http://www.scopus.com/inward/record.url?scp=0028788840&partnerID=8YFLogxK
U2 - 10.1016/0040-4039(95)01915-5
DO - 10.1016/0040-4039(95)01915-5
M3 - Article
AN - SCOPUS:0028788840
VL - 36
SP - 8771
EP - 8774
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 48
ER -