ChemInform Abstract: (+)-Sparteine-Mediated Substitution of o-Benzyl-N-pivaloylaniline with Ketones

The (+)-sparteine-mediated lithiation–substitution of o-benzyl-N-pivaloylaniline with various ketones was investigated. The obtained highly enantioenriched tertiary alcohols were used for the synthesis of alkenyl-substituted products 12 and 13 as well as 3,3,4-trisubstituted tetrahydroquinoline derivatives 22–24. The reaction with α,β-unsaturated ketones afforded highly enantioenriched 1,4-addition products 28–33 and provided a protocol for the asymmetric synthesis of highly substituted tetralin derivative 34.