Π-Face Diastereoselection: Stereochemistry and Reactivity of Addition Reactions on Conformationally Rigid Substrates: 5-X-Adamantan-2-ones and trans-10-X-Decal-2-ones

Stereochemistry and relative rates k ax and k eq of addition reactions on title compounds have been measured under eight different reaction conditions (MeMgI in Et 2O and C 6H 6, MeMgCl in THF, MeLi at 20 and −78°C, Me 2Zn in Et 2O, Me 3Al in the ratio 1:1 reactant:substrate in toluene and Me 2CuLi/...

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Bibliographic Details
Published in:Tetrahedron 2000-09, Vol.56 (37), p.7237-7243
Main Authors: Di Maio, Giorgio, Solito, Gianfranco, Rosaria Varı̀, Maria, Vecchi, Elisabetta
Format: Article
Language:English
Subjects:
5-X-adamantan-2-ones
addition reactions
kinetics
π-face diastereoselection
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Summary:Stereochemistry and relative rates k ax and k eq of addition reactions on title compounds have been measured under eight different reaction conditions (MeMgI in Et 2O and C 6H 6, MeMgCl in THF, MeLi at 20 and −78°C, Me 2Zn in Et 2O, Me 3Al in the ratio 1:1 reactant:substrate in toluene and Me 2CuLi/MeLi in Et 2O at −78°C). Our kinetic data do not fit with current theories of π-face diastereoselection.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00594-9