STEREOCONTROLLED ELABORATION OF QUATERNARY CARBON CENTERS INVOLVING THE ASYMMETRIC MICHAEL-TYPE ALKYLATION OF CHIRAL IMINES - AN EFFICIENT ENANTIOSELECTIVE ACCESS TO (-VINCAMINE())

Authors
ALVES JCF SIMAS ABC COSTA PRR DANGELO J
Citation
Jcf. Alves et al., STEREOCONTROLLED ELABORATION OF QUATERNARY CARBON CENTERS INVOLVING THE ASYMMETRIC MICHAEL-TYPE ALKYLATION OF CHIRAL IMINES - AN EFFICIENT ENANTIOSELECTIVE ACCESS TO (-VINCAMINE()), Tetrahedron : asymmetry, 8(12), 1997, pp. 1963-1966
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
12
Year of publication
1997
Pages
1963 - 1966
Database
ISI
SICI code
0957-4166(1997)8:12<1963:SEOQCC>2.0.ZU;2-M
Abstract
Michael adduct (S)-5b, resulting from the condensation of chiral imine 4 with methyl acrylate, was transformed in two steps into lactone (S) -8b. Tryptamine-induced ring-opening of this lactone gave 9, which was finally converted in three steps into the key tricyclic derivative (S )-11b, a known precursor of (+)-vincamine 1. (C) 1997 Published by Els evier Science Ltd.