Tetrahedron

Influence of steric parameters on the synthesis of tetramates from α-amino-β-alkoxy-esters and Ph 3 PCCO

…, N Park, K Kempf, C Jagusch, R Schobert, S Laschat

文献索引：Loke, Inga; Park, Natja; Kempf, Karl; Jagusch, Carsten; Schobert, Rainer; Laschat, Sabine Tetrahedron, 2012 , vol. 68, # 2 p. 697 - 704

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被引用次数: 10

摘要

α-Aminoesters react with Ph3PCCO in a domino addition–Wittig cyclization sequence affording enantiomerically pure tetramates. In the case of β-oxo functionalized α- aminoesters, eg, esters of serine, threonine or β-hydroxyornithine the yields of this reaction depend heavily on the bulkiness of the β-OR group and on the configuration of β-carbon atom C-3. Smaller residues and 2R/3R-configured aminoesters give better yields. The ...