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Conformationally restricted nonchiral pipecolic acid analogues
Dmytro S Radchenko1, Nataliya Kopylova, Oleksandr O Grygorenko
1Department of Chemistry, Kyiv National Taras Shevchenko University, Volodymyrska Street 64, Kyiv 01033, Ukraine.
Abstract:
Practical syntheses of 2-azabicyclo[3.1.1]heptane-1-carboxylic (2,4-methanopipecolic), 2-azabicyclo[2.2.2]octane-1-carboxylic (2,5-ethanopipecolic), and 9-azabicyclo[3.3.1]nonane-1-carboxylic (2,6-propanopipecolic) acids are reported. The synthetic schemes are short (five, seven, and five steps, respectively) and result in reasonably high yields of the title compounds. The key step in the syntheses is the tandem Strecker reaction and intramolecular nucleophilic cyclization of ketones possessing a leaving group at the delta-position.
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