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Synlett 2007(3): 0460-0464
DOI: 10.1055/s-2007-968029
DOI: 10.1055/s-2007-968029
LETTER
© Georg Thieme Verlag Stuttgart · New York
Asymmetric Synthesis of Conformationally Constrained trans-2,3-Piperidinedicarboxylic Acid Derivatives
Weitere Informationen
Received
8 August 2006
Publikationsdatum:
07. Februar 2007 (online)
Publikationsverlauf
Publikationsdatum:
07. Februar 2007 (online)
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Abstract
An efficient asymmetric synthesis of conformationally constrained (2S,3S)-piperidinedicarboxylic acid derivatives starting from l-aspartic acid β-tert-butyl ester and 3-chloro-2-(chloromethyl)-1-propene is described. The key steps involve N-alkylation of the aspartic acid ester followed by a stereoselective enolate intramolecular cyclization (>95:5 dr). Various synthetic strategies were explored to achieve the cyclopropanation of the resulting olefin, including the Simmons-Smith reaction and palladium-catalyzed cyclopropanation.
Key words
cyclopropanation - allylic amine - Simmons-Smith reagent - asymmetric synthesis - spiro piperidine
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