II-face diastereoselection: Stereochemistry and reactivity of addition reactions on conformationally rigid substrates: 5-X-adamantan-2-ones and trans-10-X-decal-2-ones

Authors
Di Maio, G Solito, G Vari, MR Vecchi, E
Citation
G. Di Maio et al., II-face diastereoselection: Stereochemistry and reactivity of addition reactions on conformationally rigid substrates: 5-X-adamantan-2-ones and trans-10-X-decal-2-ones, TETRAHEDRON, 56(37), 2000, pp. 7237-7243
Citations number
30
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
37
Year of publication
2000
Pages
7237 - 7243
Database
ISI
SICI code
0040-4020(20000908)56:37<7237:IDSARO>2.0.ZU;2-N
Abstract
Stereochemistry and relative rate a k(ax) and k(eq) of addition reactions o n title compounds have been measured under eight different reaction conditi ons (MeMgI in Et2O and C6H6, MeMgCl in THF, MeLi at 20 and -78 degrees C, M e2Zn in Et2O, Me3Al in the ratio 1:1 reactant:substrate in toluene and Me2C uLi/MeLi in Et2O at -78 degrees C). Our kinetic data do not fie with curren t theories of rr-face diastereoselection. (C) 2000 Elsevier Science Ltd. Al l rights reserved.