Thermodynamic enolate formation

2 real reactions from the literature, on six-membered cyclic ketones. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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1. Thermodynamic enolate formation: 2-methylcyclohexanone (a six-membered cyclic ketone) with 1) 1.05 eq KH / RT; 2) add BEt3; 1) 1.05 eq KN(SiMe3)2 -78 C; 2) add BEt3 gives the thermodynamic enolate.

   Thermodynamic enolate formationTetrahedron Lett. 1983, 24, 1341

2. Thermodynamic enolate formation: 2-(1,3-benzodioxol-5-yl)cyclohexan-1-one (a six-membered cyclic ketone) with 1) Et3N, TMSCl; 2) MeLi gives the thermodynamic enolate.

   Thermodynamic enolate formationJ. Org. Chem. 2005, 70, 6523