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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Cheung, Lawrence L. W. Yudin, Andrei K. |
| Description | Author Affiliation: Cheung LL ( Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George St., Toronto ON, M5S 3H6, Canada.) |
| Abstract | In this contribution, aminocyclobutanes, as well as eight-membered enamide rings, have been made from N-vinyl β-lactams. The eight-membered products have been formed by a [3,3]-sigmatropic rearrangement, whereas the aminocyclobutanes have been derived from a domino [3,3]-rearrangement/6π-electrocyclisation process. The aminocyclobutanes have been obtained in a highly diastereoselective fashion. The cyclobutane ring system tolerates fusion even if adjacent quaternary centres are present. Systems containing up to four fused rings are readily accessible. The reaction profile has been investigated by using Gaussian 03. This study suggests that two reaction pathways for aminocyclobutane formation are possible. In one pathway the [3,3]-sigmatropic rearrangement is the rate-limiting step and in the second pathway the electrocyclisation is rate limiting. Taken together, these reactions should facilitate the construction of fused heterocycles. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 13 |
| Volume Number | 16 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2010-04-06 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Cyclobutanes Chemical Synthesis Vinyl Compounds Chemistry Beta-Lactams Catalysis Crystallography, X-Ray Cyclization Molecular Structure Stereoisomerism Structure-Activity Relationship Research Support, Non-U.S. Gov't |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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