Abstract
Thermal reactions of 1,2,3-trisubstituted ariridines 1 with 1,3-thiazole-5(4H)-thiones 6 in toluene yielded, in general, a mixture of two diastereoisomeric spirocyclic [2+3] cycloadducts. The formation of these products can be explained by a stereoselective electrocyclic ring opening of 1 to give an azomethine ylide 2 as the reactive intermediate, which is trapped immediately by 6 via a stereoselective 1,3-dipolar cycloaddition. Only in the case of trans-dimethyl 1-(4-methoxyphenyl)aziridine-2,3-dicarboxylate (trans-la), four diastereoisomeric cycloadducts were formed (Scheme 4). This result is rationalized by an isomerization of the intermediate azomethine ylide cis-2a to trans-2a.
| Item Type: | Journal Article, refereed, original work |
|---|
| Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
|---|
| Dewey Decimal Classification: | 540 Chemistry |
|---|
| Scopus Subject Areas: | Physical Sciences > Catalysis
Life Sciences > Biochemistry
Life Sciences > Drug Discovery
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Physical Sciences > Inorganic Chemistry |
|---|
| Uncontrolled Keywords: | Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis |
|---|
| Language: | English |
|---|
| Date: | 1998 |
|---|
| Deposited On: | 12 Nov 2013 14:05 |
|---|
| Last Modified: | 10 Mar 2025 02:37 |
|---|
| Publisher: | Wiley-Blackwell |
|---|
| ISSN: | 0018-019X |
|---|
| Funders: | Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel, Swiss Federal Commission for Foreign Students (Bundesstipendiat) |
|---|
| OA Status: | Closed |
|---|
| Publisher DOI: | https://doi.org/10.1002/hlca.19980810309 |
|---|
| Project Information: | - Funder: SNSF
- Grant ID:
- Project Title: Swiss National Science Foundation
- Funder:
- Grant ID:
- Project Title: F. Hoffmann-La Roche AG, Basel
- Funder:
- Grant ID:
- Project Title: Swiss Federal Commission for Foreign Students (Bundesstipendiat)
|
|---|
Mlostoń, Grzegorz