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.

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

MENINNO, SARA;LATTANZI, Alessandra;DELLA SALA, Giorgio
2015

Abstract

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.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11386/4651386
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