ChemInform Abstract: Highly Enantioselective Synthesis of Pipecolic Acid Derivatives via an Asymmetric Aza-Diels-Alder Reaction

Autor:	Timothy C. Hancox, Patrick D. Bailey, Andrew B. Holmes, Derek J. Londesbrough, John D. Heffernan
Rok vydání:	2010
Předmět:	chemistry.chemical_compound chemistry Yield (chemistry) Imine Enantioselective synthesis Trifluoroacetic acid chemistry.chemical_element Aza-Diels–Alder reaction General Medicine Nitrogen Medicinal chemistry Asymmetric induction Pipecolic acid
Zdroj:	ChemInform. 26
ISSN:	0931-7597
DOI:	10.1002/chin.199517142
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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