Total facial selectivity of a D-erythrosyl aromatic imine in [4 pi+2 pi] cycloadditions; synthesis of 2-alkylpolyol 1,2,3,4-tetrahydroquinolines

• Type: Article in International Scientific Journal
• Date: 2016

Authors

Ferreira, J (Author) Other; Duarte, VCM (Author) FEUP; Noro, J (Author) Other; Fortes, AG (Author) Other; Alves, MJ (Author) Other

Journal

Title: Organic and Biomolecular Chemistry

Vol. 14

Pages: 2930-2937

ISSN: 1477-0520

Publisher: Royal Society of Chemistry

Indexing

ISI Web of Knowledge - 2 Citations

Scopus - 3 Citations

Other information

Authenticus ID: P-00K-8J7

DOI: 10.1039/c5ob02594j

Abstract (EN): Different electron-rich dienophiles were combined with the imine obtained from 2,4-O-benzylidene-D-erythrose and p-anisidine furnishing enantiomerically pure tetrahydroquinolines, by inverse electron-demand [4 pi + 2 pi] cycloaddition. The imine was also reacted with 2-substituted electron-rich 1,3-butadienes giving the diastereomeric pure product, resulting from the normal electron demand cycloaddition. The facial selectivity of both processes is proposed on the basis of a 1,4-relationship between the hydroxyl group and the nitrogen atom in the chiral N-(p-methoxyphenyl) imine derivative.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 8