SUGAROMETALLIC CHEMISTRY - AGLYCONE-CHROMIUM COMPLEX AS CHIRAL AUXILIARY IN ASYMMETRIC DIELS-ALDER REACTION

Authors
SHING TKM CHOW HF CHUNG IHF
Citation
Tkm. Shing et al., SUGAROMETALLIC CHEMISTRY - AGLYCONE-CHROMIUM COMPLEX AS CHIRAL AUXILIARY IN ASYMMETRIC DIELS-ALDER REACTION, Tetrahedron letters, 37(21), 1996, pp. 3713-3716
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
21
Year of publication
1996
Pages
3713 - 3716
Database
ISI
SICI code
0040-4039(1996)37:21<3713:SC-ACA>2.0.ZU;2-I
Abstract
The diastereoselectivity of the the Diels-Alder reaction of eta(6)-(4' -methylbenzyl oyl-3,4-O-isopropylidene-beta-L-arabinopyranoside) trica rbonylchromium(O) 5 with isoprene, butadiene, cyclopentadiene, and fur an were studied, and the best selectivity was 95:5 (with isoprene), wh ereas the diastereoselectivity of the same reaction with the noncomple xed chiral auxiliary-acrylate 6 was only 78:22. The absolute configura tion of the newly generated stereogenic center was Sound to be R in ea ch case. Copyright (C) 1996 Elsevier Science Ltd