Asymmetric Synthesis of β2‐homo‐tert‐Leucine via Radical Addition to Enantiopure N‐Fumaroylhexahydrobenzooxazolidin‐2‐one |
| |
Authors: | Margarita Escudero‐Casao Eusebio Juaristi |
| |
Institution: | Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado Postal 14‐740, México D.?F. 07000, México |
| |
Abstract: | β‐Amino acids are key structural elements in unnatural peptides, peptidomimetics, and many other physiologically active compounds. In view of their importance, we have developed an efficient synthetic route that provides highly enantiomerically enriched (R)‐ and (S)‐H‐β2‐htLeu‐OH via highly diastereo‐ and regioselective addition of tert‐butyl radical to enantiomerically pure N‐fumaroyloxazolidinones, followed by removal of the chiral auxiliary, Curtius rearrangement, ester hydrolysis, and catalytic hydrogenolysis. |
| |
Keywords: | Amino acids tert‐Butyl radical Diastereoselective addition Oxazolidinones Chiral auxiliaries |
|
|