Tetrahedron letters

The first asymmetric synthesis of (2S, 3S, 4R)-3-amino-2-hydroxymethyl-4-hydroxypyrrolidine

KL Curtis, J Fawcett, S Handa

文献索引：Curtis, Kim L.; Fawcett, John; Handa, Sandeep Tetrahedron Letters, 2005 , vol. 46, # 32 p. 5297 - 5300

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被引用次数: 18

摘要

The novel (2S, 3S, 4R)-3-amino-2-hydroxymethyl-4-hydroxypyrrolidine 5 has been produced in an efficient synthesis from trans-4-hydroxy-l-proline 8. The key step involves a tethered aminohydroxylation of the alkene 7 to introduce regio-and stereoselectively the amino alcohol functionality in the resulting products 6 and 13. Subsequent deprotection steps furnish the target molecule 5 as well as several differentially protected analogues.