The stereoselective addition of aryl- and alkylacetylene derivatives to imines was studied. The reaction is catalyzed by copper complexes of enantiomerically pure bisimines, readily prepared in very high yields from the commercially available binaphthyl diamine. A very simple experimental procedure allowed to obtain at room temperature optically active propargylamines in high yields and enantioselectivity. Interestingly, bisimine/copper(I) complexes were able to promote the direct, enantioselective, catalytic addition to imines of alkylacetylenes. The effects of catalyst loading and other reaction parameters on the stereochemical outcome of the transformation were investigated. The extremely convenient methodology, the mild reaction conditions, and the possibility of a modular approach for developing new and more efficient bisimine-based chiral ligands make the present methodology very attractive.

Very mild, enantioselective synthesis of propargylamines catalyzed by copper(I)-bisimine complexes / F. Colombo, M. Benaglia, S. Orlandi, F. Usuelli, G. Celentano. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 71:5(2006), pp. 2064-2070.

Very mild, enantioselective synthesis of propargylamines catalyzed by copper(I)-bisimine complexes

F. Colombo
Primo
;
M. Benaglia
Secondo
;
S. Orlandi;G. Celentano
Ultimo
2006

Abstract

The stereoselective addition of aryl- and alkylacetylene derivatives to imines was studied. The reaction is catalyzed by copper complexes of enantiomerically pure bisimines, readily prepared in very high yields from the commercially available binaphthyl diamine. A very simple experimental procedure allowed to obtain at room temperature optically active propargylamines in high yields and enantioselectivity. Interestingly, bisimine/copper(I) complexes were able to promote the direct, enantioselective, catalytic addition to imines of alkylacetylenes. The effects of catalyst loading and other reaction parameters on the stereochemical outcome of the transformation were investigated. The extremely convenient methodology, the mild reaction conditions, and the possibility of a modular approach for developing new and more efficient bisimine-based chiral ligands make the present methodology very attractive.
in-situ generation; terminal alkynes; direct-addition; organometallic reagents; cycloaddition reactions; asymmetric catalysis; copper-complexes; ionic liquids; schiff-bases; ligands
Settore CHIM/06 - Chimica Organica
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/32866
Citazioni
  • ???jsp.display-item.citation.pmc??? 4
  • Scopus 117
  • ???jsp.display-item.citation.isi??? 113
social impact