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
E. Manoni, A. Gualandi, L. Mengozzi, M. Bandini, P. G. Cozzi (2015). Organocatalytic enantioselective synthesis of 1-vinyl tetrahydroisoquinolines through allenamide activation with chiral Bronsted acids. RSC ADVANCES, 5, 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.
