ORIGINS OF DIASTEREOSELECTIVITY IN THE ALKYLATION OF N-SUBSTITUTED LACTAMS AND AMIDES DERIVED FROM OPTICALLY-ACTIVE AMINOALCOHOLS

Authors
MICOUIN L JULLIAN V QUIRION JC HUSSON HP
Citation
L. Micouin et al., ORIGINS OF DIASTEREOSELECTIVITY IN THE ALKYLATION OF N-SUBSTITUTED LACTAMS AND AMIDES DERIVED FROM OPTICALLY-ACTIVE AMINOALCOHOLS, Tetrahedron : asymmetry, 7(10), 1996, pp. 2839-2846
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
10
Year of publication
1996
Pages
2839 - 2846
Database
ISI
SICI code
0957-4166(1996)7:10<2839:OODITA>2.0.ZU;2-T
Abstract
The origins of diastereoselectivity in the alkylation of lactams la an d Ib and amides 6a and 6b are discussed. A rigid intermediate in which the pyramidalized amide nitrogen chelated the alkoxide lithium cation is invoked. Further experiments conducted with different substrates' are in agreement with the proposed model, Furthermore this model can e xplain the differences observed previously between ephedrine and pseud oephedrine amide alkylation. Copyright (C) 1996 Elsevier Science Ltd