TY - JOUR
T1 - Highly enantioselective synthesis of pipecolic acid derivatives via an asymmetric aza-Diels-Alder reaction
AU - Bailey, Patrick D.
AU - Londesbrough, Derek J.
AU - Hancox, Timothy C.
AU - Heffernan, John D.
AU - Holmes, Andrew B.
PY - 1994
Y1 - 1994
N2 - 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%).
AB - 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%).
UR - http://www.scopus.com/inward/record.url?scp=37049082371&partnerID=8YFLogxK
U2 - 10.1039/C39940002543
DO - 10.1039/C39940002543
M3 - Article
SN - 0022-4936
SP - 2543
EP - 2544
JO - Journal of the Chemical Society, Chemical Communications
JF - Journal of the Chemical Society, Chemical Communications
IS - 22
ER -