n this paper we present a new approach for the realization of tetrahydroisoquinoline scaffolds via stereoselective proto-activation of suitable allenamide precursors. The elusive and rather unstable iminium ion derived from acrylaldehyde is generated in situ and this electrophilic intermediate can be engaged in stereoselective intramolecular Friedel–Crafts-type allylic alkylation with electron-rich aromatic rings. The highest enantioselectivity for tetrahydroisoquinoline intermediates, obtained by organocatalytic transformation, is reported
Organocatalytic enantioselective synthesis of 1-vinyl tetrahydroisoquinolines through allenamide activation with chiral Bronsted acids / E. Manoni; A. Gualandi; L. Mengozzi; M. Bandini; P. G. Cozzi. - In: RSC ADVANCES. - ISSN 2046-2069. - ELETTRONICO. - 5:(2015), pp. 10546-10550. [10.1039/c4ra14942d]
Organocatalytic enantioselective synthesis of 1-vinyl tetrahydroisoquinolines through allenamide activation with chiral Bronsted acids
MANONI, ELISABETTA;GUALANDI, ANDREA;MENGOZZI, LUCA;BANDINI, MARCO;COZZI, PIER GIORGIO
2015
Abstract
n this paper we present a new approach for the realization of tetrahydroisoquinoline scaffolds via stereoselective proto-activation of suitable allenamide precursors. The elusive and rather unstable iminium ion derived from acrylaldehyde is generated in situ and this electrophilic intermediate can be engaged in stereoselective intramolecular Friedel–Crafts-type allylic alkylation with electron-rich aromatic rings. The highest enantioselectivity for tetrahydroisoquinoline intermediates, obtained by organocatalytic transformation, is reportedI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.