A stereselective synthesis of the title compounds, starting from commercially available amino acids, is described. The absolute stereochemistry of 3a and 3b has been deduced on the basis of H-1 NMR and chemical degradation studies. The formation of only these two isomers has been rationalized in terms of molecular mechanics calculations.
Corelli, F., Crescenza, A., Dei, D., Taddei, M., Botta, M. (1994). Cyclic Dipeptides - A Stereocontrolled Synthesis of (2s,3r,6r) and (2r,3r,6r)-6-tert-butoxycarbonylamino-3-methoxycarbonyl-2-methyl-5-oxope Rhydro-1,4-thiazepine. TETRAHEDRON-ASYMMETRY, 5(8), 1469-1472 [10.1016/0957-4166(94)80115-0].
Cyclic Dipeptides - A Stereocontrolled Synthesis of (2s,3r,6r) and (2r,3r,6r)-6-tert-butoxycarbonylamino-3-methoxycarbonyl-2-methyl-5-oxope Rhydro-1,4-thiazepine
Corelli, Federico;Taddei, Maurizio;Botta, Maurizio
1994-01-01
Abstract
A stereselective synthesis of the title compounds, starting from commercially available amino acids, is described. The absolute stereochemistry of 3a and 3b has been deduced on the basis of H-1 NMR and chemical degradation studies. The formation of only these two isomers has been rationalized in terms of molecular mechanics calculations.
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https://hdl.handle.net/11365/31203
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