A three-component stereoselective reaction between an aldehyde, an amine and phenylacetylene to afford optically active propargyl amines in good yields was developed. The reaction is catalysed by copper complexes of enantiomerically pure bis-imines. The best results were obtained with imines readily prepared in very high yields from the commercially available binaphtyl diamine. A very simple experimental procedure at room temperature allowed to obtain optically active propargyl amines in very good yields and enantioselectivity up to 75%. The extremely simple methodology and the mild reaction conditions, as well as the possibility of a modular approach for developing new and more efficient bis-imine-based chiral ligands make the present methodology very attractive.

Asymmetric multicomponent copper catalyzed synthesis of chiral propargylamines / F. COLOMBO, M. BENAGLIA, S. ORLANDI, F. USUELLI. - In: JOURNAL OF MOLECULAR CATALYSIS. A: CHEMICAL. - ISSN 1381-1169. - 260:1-2(2006), pp. 128-134.

Asymmetric multicomponent copper catalyzed synthesis of chiral propargylamines

F. COLOMBO
Primo
;
M. BENAGLIA
Secondo
;
S. ORLANDI
Penultimo
;
2006

Abstract

A three-component stereoselective reaction between an aldehyde, an amine and phenylacetylene to afford optically active propargyl amines in good yields was developed. The reaction is catalysed by copper complexes of enantiomerically pure bis-imines. The best results were obtained with imines readily prepared in very high yields from the commercially available binaphtyl diamine. A very simple experimental procedure at room temperature allowed to obtain optically active propargyl amines in very good yields and enantioselectivity up to 75%. The extremely simple methodology and the mild reaction conditions, as well as the possibility of a modular approach for developing new and more efficient bis-imine-based chiral ligands make the present methodology very attractive.
multicomponent reactions ; chiral copper(I) complexes ; asymmetric catalysis ; phenylacetylene addition ; chiral propargylamines
Settore CHIM/06 - Chimica Organica
http://scienceserver.cilea.it/pdflinks/07060612023612518.pdf
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/32875
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