Dirscherl, Georg and Rooshenas, Parham and Schreiner, Peter R. and Lamaty, Frederic and Koenig, Burkhard (2008) Synthesis and structure of a heterocyclic ansa pyrrole amino acid. TETRAHEDRON, 64 (13). pp. 3005-3016. ISSN 0040-4020,
Full text not available from this repository. (Request a copy)Abstract
We report a synthetic route to ansa pyrrole amino acids via olefin ring-closing metathesis of diene precursors in the presence of Grubbs I catalyst. The dienes were prepared by Grignard addition to pyrrole sulfinyl imines. The success of the macrocyclic ring closure depends oil the dienes structure and only in the case of the 13-membered compound 28 sufficient material could be isolated by preparative HPLC separation to investigate its structure spectroscopically. As also rationalized by our computations at the B3LYP/6-311+G(d,p)//B3LYP/6-31G(d) level of theory, 28 is configurationally stable. (C) 2008 Elsevier Ltd. All rights reserved.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | RING-CLOSING METATHESIS; OLEFIN CROSS-METATHESIS; ASYMMETRIC-SYNTHESIS; ORGANIC-SYNTHESIS; ORGANOMETALLIC REAGENTS; TERT-BUTANESULFINIMINES; REVERSIBLE NATURE; COMPLEXES; CYCLOPHANES; DENSITY; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 05 Nov 2020 10:31 |
| Last Modified: | 05 Nov 2020 10:31 |
| URI: | https://pred.uni-regensburg.de/id/eprint/31168 |
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