π-Face diastereoselection: Stereochemistry and reactivity of reduction reactions on conformationally rigid substrates: 5-X-adamantan-2-ones and trans-10-X-decal-2-ones

作者: Giorgio Di Maio , Gianfranco Solito , Maria Rosaria Varı̀ , Elisabetta Vecchi

DOI: 10.1016/S0040-4020(00)00594-9

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摘要: Abstract Stereochemistry and relative rates kax keq of addition reactions on title compounds have been measured under eight different reaction conditions (MeMgI in Et2O C6H6, MeMgCl THF, MeLi at 20 −78°C, Me2Zn Et2O, Me3Al the ratio 1:1 reactant:substrate toluene Me2CuLi/MeLi −78°C). Our kinetic data do not fit with current theories π-face diastereoselection.

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