Asymmetric synthesis of intermediates for otamixaban and premafloxacin by the chiral ligand-controlled asymmetric conjugate addition of a lithium amide.
Asymmetric synthesis of intermediates for otamixaban and premafloxacin by the chiral ligand-controlled asymmetric conjugate addition of a lithium amide.
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DOI：
10.1021/jo060588d
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发表时间：
2006-05
期刊：
影响因子：
--
通讯作者：
Takeo Sakai;Y. Kawamoto;K. Tomioka
中科院分区：
文献类型：
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作者：
Takeo Sakai;Y. Kawamoto;K. Tomioka
苄基（三甲基硅基）氨基锂与叔丁基烯酸酯通过手性配体控制的共轭加成反应合成了相应的烯醇锂，再与亲电试剂反应，得到了ee高达98%的抗烷基化产物.通过仲胺氧化成亚胺，再经酰亚胺化反应除去氨基氮上的苄基，得到3-氨基烷酸酯，产率较高。该产物可能是合成奥米沙班和普瑞马沙星的关键中间体。
A chiral ligand-controlled conjugate addition reaction of lithium benzyl(trimethylsilyl)amide with tert-butyl enoates gave the corresponding lithium enolates that were then treated with electrophiles, giving anti-alkylation products with high ee up to 98%. The benzyl group on the amino nitrogen was removed by the oxidation of secondary amines to imines and subsequent transoximation to give 3-aminoalkanoates in good yields. The products are the possible key intermediates of otamixaban and premafloxacin.