A scalable synthesis of (1R,3S,5R)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-car b oxylic acid

A scalable synthesis of (1R,3S,5R)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-car b oxylic acid

A stereoselective and scalable synthesis of (1R,3S,5R)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-car b oxylic 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...

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Veröffentlicht in:Tetrahedron letters 2013-12, Vol.54 (49), p.6722-6724
Hauptverfasser: Wang, Gan, James, Clint, Meanwell, Nicholas, Hamann, Lawrence, Belema, Makonen
Format: Artikel
Sprache:eng
Schlagworte:
Functional groups
Stereoselectivity
Synthesis (chemistry)
Tetrahedrons
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Zusammenfassung:A stereoselective and scalable synthesis of (1R,3S,5R)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-car b oxylic 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-I-.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2013.09.114