pi-face diastereoselection: stereochemistry and reactivity of reduction reactions on conformationally rigid substrates: 5-X-adamantan-2-ones and trans-10-X-decal-2-ones

Authors
Di Maio, G Innella, C Vecchi, E
Citation
G. Di Maio et al., pi-face diastereoselection: stereochemistry and reactivity of reduction reactions on conformationally rigid substrates: 5-X-adamantan-2-ones and trans-10-X-decal-2-ones, TETRAHEDRON, 57(34), 2001, pp. 7403-7407
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
34
Year of publication
2001
Pages
7403 - 7407
Database
ISI
SICI code
0040-4020(20010820)57:34<7403:PDSARO>2.0.ZU;2-K
Abstract
Stereochemistry and relative rates k(ax) and k(eq) of reduction reactions o n title compounds have been measured under four different reaction conditio ns (NaBH4 in i-PrOH, LiBH4 and NaAlH4 in THF and LiAlH4 in Et2O). Reaction sensitivities show that the Group III element has a prominent role in deter mining the structure of the transition state shape. (C) 2001 Elsevier Scien ce Ltd. All rights reserved.