在催化不对称的亚齐里迪纳化中进行受控的立体和立体选择
Aman A Desai1, William D Wulff
1Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
Journal of the American Chemical Society
|September 3, 2010
概括
布伦斯特酸催化剂能够实现不对称的亚齐里迪纳. 这项研究证明了它们与二乙胺一起用于产生跨亚齐里丁,扩展了通用催化不对称的亚齐里丁化协议.
科学领域:
- 有机化学 有机化学
- 不对称的催化剂.
- 合成方法论 合成方法论
背景情况:
- 从VANOL和VAPOL连接体中衍生出来的基拉尔聚酸布伦斯特德酸是合成cis-aziridines的已知催化剂.
- 这些催化剂调解了二甲基胺和二 Ester 之间的反应.
研究的目的:
- 为了研究性多酸Brønsted酸与二乙胺的催化活性.
- 为cis-和trans-aziridines开发一个通用的催化不对称的阿齐里迪纳协议.
主要方法:
- 使用从VANOL和VAPOL配体中制备的奇拉聚酸布伦斯特德酸催化剂.
- 通过与二乙胺的二甲基伊胺反应,形成跨亚齐里丁.
- 分析基质范围包括芳香性和性化物.
主要成果:
- 性聚酸盐催化剂成功地调解了从imines和diazoacetamides中形成的跨亚齐里丁,具有高不对称的诱导.
- 反应表现出广泛的基质范围,容纳各种芳香性和性化物.
- 面选择性独立于二化合物, (S) - VANOL/(S) - VAPOL催化剂指导添加到cis-aziridines的Si-面和trans-aziridines的Re-面.
结论:
- 已经建立了一个通用的催化不对称的亚齐里迪纳化协议,可以容纳二氧和二氧胺.
- 开发的方法为合成cis-和trans-aziridines提供了高度的立体化学控制.
- 这项工作扩大了在不对称合成中性多酸布伦斯特德酸催化剂的合成实用性.
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