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A scalable synthesis of (1R,3S,5R)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid |
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| Authors: | Gan Wang Clint A. JamesNicholas A. Meanwell Lawrence G. HamannMakonen Belema |
| Affiliation: | Department of Discovery Chemistry, Bristol-Myers Squibb Research & Development, 5 Research Parkway, Wallingford, CT 06492, USA |
| Abstract: | A stereoselective and scalable synthesis of (1R,3S,5R)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid (3a) is described. Key to the success of the devised route was the realization that the stereoselectivity of a cyclopropanation step could be controlled by the composition of the functional group at C-α. |
| Keywords: | Cyclopropanation Epimerization Equilibration Methanoproline Oxidative decarboxylation |
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