4-Formylazetidin-2-ones, Synthonfor the Facile Synthesis of Enantiopure 4-Aminopiperidin-2-ones

Devanathan Krishnaswamy; Vidyesh V. Govande; Abdul Rakeeb A. S. Deshmukh

doi:10.1055/s-2003-40979

PAPER

4-Formylazetidin-2-ones, Synthonfor the Facile Synthesis of Enantiopure 4-Aminopiperidin-2-ones

Devanathan Krishnaswamy, Vidyesh V. Govande, Abdul Rakeeb A. S. Deshmukh*
Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411008, India
Fax: +91(20)5893153; e-Mail: arasd@dalton.ncl.res.in;

Abstract

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Abstract

Enantiopure 4-formylazetidin-2-ones 1a-d have been used as building blocks forthe synthesis of 4-aminopiperidin-2-ones 6a-d in 28-39% overall yields.The synthesis involves ring expansion of azetidinone 4a-d via methanolysis followed by a reductivecyclization of the C-4 nitroethyl side chain with an ester group.

Key words

lactams - reductions - cyclizations - aldolreactions - piperidines - esters

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Referenzen

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