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Concise synthesis of all four stereoisomers of 3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

Furegati, Markus and Ossola, Flavio and La Vecchia, Luigi and Kramer, Christian and Bakonyi, Bettina (2013) Concise synthesis of all four stereoisomers of 3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid. Journal of Organic Chemistry, 78 (18). pp. 9328-9339.

Abstract

A concise synthesis of all four stereoisomers of 3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid has been developed; thereby significantly shortening the known literature procedures for the syntheses of these unnatural amino acids. With a simple adjustment of the reaction conditions, we were able to obtain either pure cis or trans acid. Optical resolution was accomplished via diastereomeric salt formation or alternatively via chromatography on a chiral stationary phase. Finally, ab-initio calculations gave an explanation for the observed cis selectivity in the initial step.

Item Type: Article
Additional Information: Bettina Bakonyi: Former bachelor student from the Fachhochschule in Muttenz, working 3 months on this project. Christian Kramer: Former postdoc at GDC. During this time he performed the ab-initio part of the present article but not as part of his postdoctoral project.
Keywords: scale-up, lithiation, diastereomeric salt formation, flow, ab-initio
Date Deposited: 26 Apr 2016 23:46
Last Modified: 26 Apr 2016 23:46
URI: https://oak.novartis.com/id/eprint/10458

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