An efficient asymmetric synthesis of -sulfinylamino isocyanides is reported on the basis of the highly diastereoselective addition of 9-isocyanofluorene to optically pure N-tert-butanesulfinimines. The resulting optically pure isocyanides readily cyclized to give optically pure 2-imidazolines upon removal of the sulfinyl group. Furthermore, the -sulfinylamino isocyanides were used as chiral inputs in Ugi and Passerini multicomponent reactions to generate new types of (pseudo)peptide scaffolds. Optically pure -sulfinylamino isocyanides are synthesized in a highly diastereoselective addition of 9-isocyanofluorene with N-tert-butanesulfinimines. Follow-up chemistry demonstrates that they are excellent precursors for the preparation of optically pure 2-imidazolines. Furthermore, they are applied in Ugi and Passerini multicomponent reactions; TMSOTf = trimethylsilyl trifluoromethanesulfonate, DIPEA = N,N- diisopropylethylamine. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
|Journal||European Journal of Organic Chemistry|
|Publication status||Published - 2014|
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CCDC 988359: Experimental Crystal Structure Determination
Janssen, G. V. (Contributor), Vicente-García, E. (Contributor), Vogel, W. (Contributor), Slootweg, J. C. (Contributor), Ruijter, E. (Contributor), Lammertsma, K. (Contributor) & Orru, R. V. A. (Contributor), Unknown Publisher, 1 Jan 2014
DOI: 10.5517/cc125gk8, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc125gk8&sid=DataCite