Very high asymmetric induction is observed in the aza-Diels-Alder reaction between dienes and the imine (R)-PhMeCH-N=CHCO2PhMen* (where PhMen* = 8-phenylmenthyl), which bears matched auxiliaries on nitrogen and on the ester; reactions in trifluoroethanol, in the presence of trifluoroacetic acid (1 equiv.), give substituted pipecolic acid derivatives in ca 50% isolated yield, with only a single regio- and diastereo-isomer of the cycloadduct detectable in all cases (d.e.>95%).
|Number of pages||2|
|Journal||Journal of the Chemical Society, Chemical Communications|
|Publication status||Published - 1994|