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