Weber, Anna K. and Schachtner, Josef and Fichtler, Robert and Leermann, Timo M. and Neudoerfl, Joerg M. and Jacobi von Wangelin, Axel (2014) Modular synthesis of cyclic cis- and trans-1,2-diamine derivatives. ORGANIC & BIOMOLECULAR CHEMISTRY, 12 (28). pp. 5267-5277. ISSN 1477-0520, 1477-0539
Full text not available from this repository. (Request a copy)Abstract
Structurally diverse carbocycles with two vicinal nitrogen-substituents were prepared in expedient three-component reactions from simple amines, aldehydes, and nitroalkenes. trans, trans-6-Nitrocyclohex-2-enyl amines were obtained in a one-pot domino reaction involving condensation, tautomerisation, conjugate addition, and nitro-Mannich cyclisation. Upon employment of less nucleophilic carboxamides, a concerted Diels-Alder cycloaddition mechanism operated to give the corresponding cis, trans-nitrocyclohexenyl amides. Both types of substituted carbocycles offer ample opportunities for chemical manipulations at the core and periphery. Ring oxidation with MnO2 affords substituted nitroarenes. Reduction with Zn/HCl provides access to various trans-and cis-diaminocyclohexenes, respectively, in a straight-forward manner. With enantiopure secondary amines, a two-step synthesis of chiral nitrocyclohexadienes was developed (82-94% ee).
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | DIELS-ALDER REACTIONS; MULTICOMPONENT COUPLING REACTIONS; ONE-POT SYNTHESIS; ORGANIC-SYNTHESIS; ALPHA,BETA-UNSATURATED ALDEHYDES; OXIDATIVE AROMATIZATION; MICHAEL ADDITION; MOLECULAR-OXYGEN; CONJUGATED NITROALKENES; CYCLOADDITION REACTIONS; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Anorganische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 02 Dec 2019 08:33 |
| Last Modified: | 02 Dec 2019 08:33 |
| URI: | https://pred.uni-regensburg.de/id/eprint/10975 |
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