REMOTE ASYMMETRIC INDUCTION - SYNTHESIS OF C-LINKED ALPHA-GALACTOSERINE AND HOMOSERINE DERIVATIVES BY ELECTROPHILIC AMINATION

Authors
ARYA P BEN RN QIN HP
Citation
P. Arya et al., REMOTE ASYMMETRIC INDUCTION - SYNTHESIS OF C-LINKED ALPHA-GALACTOSERINE AND HOMOSERINE DERIVATIVES BY ELECTROPHILIC AMINATION, Tetrahedron letters, 39(34), 1998, pp. 6131-6134
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
34
Year of publication
1998
Pages
6131 - 6134
Database
ISI
SICI code
0040-4039(1998)39:34<6131:RAI-SO>2.0.ZU;2-U
Abstract
A high diastereoselectivity (98%) for electrophilic amination of compo und 9 using di-t-butyl azodicarboxyl ester as an electrophile was achi eved. A similar reaction with compound 13 having achiral oxazolidinone was studied to examine 1,4-remote asymmetric induction. In the latter , a selectivity of 6.5:1 demonstrated the effect of alpha-galactosyl m oiety, responsible for inducing the induction from the remote site. (C ) 1998 Elsevier Science Ltd. All rights reserved.