Furegati, Markus, Ossola, Flavio, La Vecchia, Luigi, 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