HIGH 1,6-DIASTEREOSELECTIVITY IN THE HYDRIDE REDUCTION OF AN ACYCLIC KETONE SUBSTRATE VIA BICYCLIC CHELATION CONTROL

Authors
ZHANG HC HARRIS BD MARYANOFF CA MARYANOFF BE
Citation
Hc. Zhang et al., HIGH 1,6-DIASTEREOSELECTIVITY IN THE HYDRIDE REDUCTION OF AN ACYCLIC KETONE SUBSTRATE VIA BICYCLIC CHELATION CONTROL, Tetrahedron letters, 37(44), 1996, pp. 7897-7900
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
44
Year of publication
1996
Pages
7897 - 7900
Database
ISI
SICI code
0040-4039(1996)37:44<7897:H1ITHR>2.0.ZU;2-Q
Abstract
Reduction of acyclic epsilon-hydroxy ketone 3 with R-Alpine-Hydride(R) in methylene chloride provided a strong preponderance of the anti dia stereomer of 4 (anti:syn = 12:1). This impressive 1,6 stereoselectivit y is attributed to bicyclic chelation control of hydride addition. Cop yright (C) 1996 Elsevier Science Ltd