Stereoselective synthesis of β-sulfinylamino isocyanides and 2-imidazolines

Autor: Janssen, G.V., Vincente-Garcia, E., Vogels, W., Slootweg, J.C., Ruijter, E., Lammertsma, K., Orru, R.V.A.
Přispěvatelé: Organic Chemistry, Computer Systems, AIMMS, Amsterdam Global Change Institute
Jazyk: angličtina
Rok vydání: 2014
Předmět:
Zdroj: Janssen, G V, Vincente-Garcia, E, Vogels, W, Slootweg, J C, Ruijter, E, Lammertsma, K & Orru, R V A 2014, ' Stereoselective synthesis of β-sulfinylamino isocyanides and 2-imidazolines ', European Journal of Organic Chemistry, vol. 2014, no. 18, pp. 3762-3766 . https://doi.org/10.1002/ejoc.201402210
European Journal of Organic Chemistry, 2014(18), 3762-3766. Wiley-VCH Verlag
ISSN: 1434-193X
DOI: 10.1002/ejoc.201402210
Popis: 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.
Databáze: OpenAIRE
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