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2005
Cyclohexane derivatives
Q 0040
Metalated Nitriles: Electrophile-Dependent Alkylations. — C-Magnesiated nitriles
electrophile-dependent stereoselective alkylation behavior not previously ob24- 073 show
served with N-metalated nitriles. Reactions with alkyl halide, sulfonate, and ketone
electrophiles proceed with retention of stereochemistry, whereas aldehyde and acyl
halide acylations proceed with inversion. Conversion of the C-metalated nitrile to the
corresponding N-metalated nitrile (cf. reactions with Me-MgBr/BuLi) permits stereodivergent alkylations. — (FLEMING*, F. F.; ZHANG, Z.; WEI, G.; STEWARD, O. W.;
Org. Lett. 7 (2005) 3, 447-449; Dep. Chem. Biochem., Duquesne Univ., Pittsburgh,
PA 15282, USA; Eng.) — Steudel
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