An efficient asymmetric synthesis of Fmoc-l-cyclopentylglycine via diastereoselective alkylation of glycine enolate equivalent |
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Authors: | Satendra Singh Michael W Pennington |
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Affiliation: | BACHEM Bioscience Inc., 3700 Horizon Drive, King of Prussia, PA 19406, USA |
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Abstract: | Stereoselective alkylation of the enolate derived from benzyl (2R,3S)-(−)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate (1) with cyclopentyl iodide afforded anti-α-monosubstituted product, benzyl (2R,3S,5S)-(−)-6-oxo-2,3-diphenyl-5-cyclopentyl-4-morpholinecarboxylate (3) in 60% yield. Catalytic hydrogenolysis over PdCl2 cleaved the auxiliary ring system to give l-cyclopentylglycine (4) in 84% yield. Subsequent protection of the α-amino function with Fmoc-OSu gave Fmoc-l-cyclopentylglycine (5) in high yield. |
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Keywords: | Fmoc- smallcaps" >l-cyclopentylglycine cyclopentylglycine glycine enolate equivalent |
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