不对称的基因胺的基化,由奇拉二醇催化
Sha Lou1, Philip N Moquist, Scott E Schaus
1Department of Chemistry and Center for Chemical Methodology and Library Development, Life Science and Engineering Building, Boston University, 24 Cummington Street, Boston, Massachusetts 02215, USA.
基拉尔BINOL衍生的二醇使得高度对乙基胺的异对称的enantioselective合. 这种方法有效合成重要的化合物,包括HIV-1药物马拉维罗克.
科学领域:
- 有机化学 有机化学
- 不对称的催化剂.
背景情况:
- 基拉尔BINOL衍生的二醇是有效的催化剂.
- 不对称的伊米因的整合是一种关键的合成挑战.
研究的目的:
- 开发一种使用奇拉BINOL衍生二醇的乙胺的异对称的enantioselective化.
- 在合成马拉维罗克时应用这种转化.
主要方法:
- 使用 (S) -3,3'-Ph2-BINOL (15 mol %) 和化二氧化的催化剂.
- 对芳香和酸乙烯胺的反应优化.
- 使用IR,NMR和质谱学的机制研究.
主要成果:
- 取得了良好的产量 (75-94%) 和高反体比 (95:5-99.5:0.5).
- 具有较高的二聚体选择性 (>98:2) 和异选择性 (>98:2) 与克罗二异氧.
- 对马拉维洛克合成的成功应用.
结论:
- 基拉尔BINOL衍生二醇是对乙烯基胺的不对称化作用的有效催化剂.
- 反应过程具有很高的立体选择性和产量.
- 这种方法提供了一个可行的途径,Maraviroc和相关化合物.
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