Asymmetric Hydroazidation of Nitroalkenes Promoted by a Secondary Amine-Thiourea Catalyst

Chiral β‐nitro azides are obtained by asymmetric addition of azides to nitroalkenes, with an enantioselectivity of up to 82% ee. The reaction, promoted by an easily accessible secondary amine‐thiourea catalyst, is performed with azidotrimethylsilane in the presence of benzoic acid. Products with dif...

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Veröffentlicht in:	Advanced synthesis & catalysis 2015-10, Vol.357 (14-15), p.3365-3373
Hauptverfasser:	Bellavista, Tiziana, Meninno, Sara, Lattanzi, Alessandra, Della Sala, Giorgio
Format:	Artikel
Sprache:	eng
Schlagworte:	Accessibility Aliphatic compounds Amines asymmetric catalysis Asymmetry azides Benzoic acid bifunctional catalysis Catalysis Catalysts Michael addition nitroolefins Synthesis
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creator	Bellavista, Tiziana Meninno, Sara Lattanzi, Alessandra Della Sala, Giorgio
description	Chiral β‐nitro azides are obtained by asymmetric addition of azides to nitroalkenes, with an enantioselectivity of up to 82% ee. The reaction, promoted by an easily accessible secondary amine‐thiourea catalyst, is performed with azidotrimethylsilane in the presence of benzoic acid. Products with different aliphatic β‐substituents are obtained in good yields and with the highest enantioselectivity reported to date. The presence of a secondary amine group was found to be crucial to achieve high stereocontrol.
doi_str_mv	10.1002/adsc.201500403
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The reaction, promoted by an easily accessible secondary amine‐thiourea catalyst, is performed with azidotrimethylsilane in the presence of benzoic acid. Products with different aliphatic β‐substituents are obtained in good yields and with the highest enantioselectivity reported to date. The presence of a secondary amine group was found to be crucial to achieve high stereocontrol.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201500403</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Accessibility ; Aliphatic compounds ; Amines ; asymmetric catalysis ; Asymmetry ; azides ; Benzoic acid ; bifunctional catalysis ; Catalysis ; Catalysts ; Michael addition ; nitroolefins ; Synthesis</subject><ispartof>Advanced synthesis & catalysis, 2015-10, Vol.357 (14-15), p.3365-3373</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. 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subjects	Accessibility Aliphatic compounds Amines asymmetric catalysis Asymmetry azides Benzoic acid bifunctional catalysis Catalysis Catalysts Michael addition nitroolefins Synthesis
title	Asymmetric Hydroazidation of Nitroalkenes Promoted by a Secondary Amine-Thiourea Catalyst
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