Highly enantioselective synthesis of pipecolic acid derivatives via an asymmetric aza-Diels–Alder reaction

Autor:	Derek J. Londesbrough, Timothy C. Hancox, Andrew B. Holmes, John D. Heffernan, Patrick D. Bailey
Rok vydání:	1994
Předmět:	chemistry.chemical_compound Chemistry Stereochemistry Yield (chemistry) Imine Enantioselective synthesis Trifluoroacetic acid Molecular Medicine Aza-Diels–Alder reaction Asymmetric induction Pipecolic acid
Zdroj:	J. Chem. Soc., Chem. Commun.. :2543-2544
ISSN:	0022-4936
DOI:	10.1039/c39940002543
Popis:	Very high asymmetric induction is observed in the aza-Diels–Alder reaction between dienes and the imine (R)-PhMeCH–NCHCO2PhMen*(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%).
Databáze:	OpenAIRE
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