Universität zu Köln

Weber, Anna K., Schachtner, Josef, Fichtler, Robert, Leermann, Timo M., Neudoerfl, Joerg M. and Jacobi von Wangelin, Axel (2014). Modular synthesis of cyclic cis- and trans-1,2-diamine derivatives. Org. Biomol. Chem., 12 (28). S. 5267 - 5278. CAMBRIDGE: ROYAL SOC CHEMISTRY. ISSN 1477-0539

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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:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Weber, Anna K. UNSPECIFIED UNSPECIFIED UNSPECIFIED Schachtner, Josef UNSPECIFIED UNSPECIFIED UNSPECIFIED Fichtler, Robert UNSPECIFIED UNSPECIFIED UNSPECIFIED Leermann, Timo M. UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg M. UNSPECIFIED UNSPECIFIED UNSPECIFIED Jacobi von Wangelin, Axel UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-450102
DOI:	10.1039/c4ob00913d
Journal or Publication Title:	Org. Biomol. Chem.
Volume:	12
Number:	28
Page Range:	S. 5267 - 5278
Date:	2014
Publisher:	ROYAL SOC CHEMISTRY
Place of Publication:	CAMBRIDGE
ISSN:	1477-0539
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language DIELS-ALDER REACTIONS; MULTICOMPONENT COUPLING REACTIONS; ONE-POT SYNTHESIS; OXIDATIVE AROMATIZATION; MICHAEL ADDITION; ALPHA,BETA-UNSATURATED ALDEHYDES; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; ACID CATALYST; SILOXY DIENES Multiple languages Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/45010