Citation
P. Szolcsanyi et al., Pd(II)-catalysed aminocarbonylation as a key step in the total synthesis of C-6 homologues of 1-deoxynojirimycin and 1-deoxy-L-idonojirimycin, TETRAHEDR-A, 11(12), 2000, pp. 2579-2597
Citations number
47
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166
→ ACNP
Volume
11
Issue
12
Year of publication
2000
Pages
2579 - 2597
Database
ISI
SICI code
0957-4166(20000630)11:12<2579:PAAAKS>2.0.ZU;2-W
Abstract
The first successful Pd(II)-catalysed aminocarbonylation of the highly subs
tituted benzylaminoalkene 5 allo ws the direct preparation of fused piperid
ine lactones 3 and 4, which are subsequently converted to the novel C-6 hom
ologue of 1-deoxynojirimycin 1 and 1-deoxy-L-idonojirimycin 2. The study of
the influence of various catalytic conditions on the diastereoselectivity
and product distribution of the key amino-carbonylation is presented. (C) 2
000 Elsevier Science Ltd. All rights reserved.