Journal of the Chemical Society. Chemical communications p. 2543 - 2544 (1994)
Update date:2022-08-03
Topics:
Bailey, Patrick D.
Londesbrough, Derek J.
Hancox, Timothy C.
Heffernan, John D.
Holmes, Andrew B.
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 50percent isolated yield, with only a single regio- and diastereo-isomer of the cycloadduct detectable in all cases (d.e. > 95percent).
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