From serine to functionalized enantiopure tetrahydroisoquinolines

Authors
Hanessian, S Demont, E van Otterlo, WAL
Citation
S. Hanessian et al., From serine to functionalized enantiopure tetrahydroisoquinolines, TETRAHEDR L, 41(26), 2000, pp. 4999-5003
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
26
Year of publication
2000
Pages
4999 - 5003
Database
ISI
SICI code
0040-4039(20000624)41:26<4999:FSTFET>2.0.ZU;2-1
Abstract
The reaction of gamma-amino-alpha,beta-unsaturated esters prepared from L-s erine with diversely substituted arylcuprates affords the corresponding syn -adducts. Transformation of the amino group to an isocyanate, followed by F riedel-Crafts intramolecular condensation, leads to enantiopure 3,4-disubst ituted tetrahydroisoquinolin-1-ones, which can be reduced to the correspond ing tetrahydroisoquinolines. (C) 2000 Elsevier Science Ltd. All rights rese rved.