与亚齐里丁酸盐一起发生的和二选择性催化化反应
Thomas A Moss1, David R Fenwick, Darren J Dixon
1School of Chemistry, The University of Manchester, Oxford Road, Manchester M13 9PL, UK.
这项研究引入了使用N-硫нил亚齐里丁的第一个不对称相移催化化. 这种方法有效地产生有价值的氨基乙烯产品,具有高的酶选择性,推进非对称合成.
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:
- 阶段转移催化 (PTC) 是一种强大的技术,可以在不混合的阶段之间实现反应.
- 非对称合成旨在创建具有高立体化学控制的奇拉分子.
- N-硫尼尔亚齐里丁是多功能合成中间体.
研究的目的:
- 开发了第一种不对称的相移催化碳酸与N-硫нил亚齐里丁的化反应.
- 为了在氨基乙烯衍生物的合成中获得高产量和酶选择性.
主要方法:
- 采用 cinchona 衍生的四级盐作为奇拉相转移催化剂.
- 采用N-o- ((三甲) 硫尼尔亚齐里丁作为电爱体.
- 在温和的基本条件下与各种碳酸 (pronucleophiles) 进行反应.
主要成果:
- 实现了N-硫нил亚齐里丁的高效环开放,产生氨基乙烯产物.
- 使用 10 mol % 催化剂,获得高产量和反选择性 (高达 97% ee).
- 从enantiopure亚齐里丁中生产出具有高产量和二元选择性 (高达30:1 dr) 的enantiopure化产品.
结论:
- 建立了一种新且高效的非对称相移催化化N-硫烯亚齐里丁的方法.
- 证明了这种方法在合成基丰富氨基乙烯化合物的实用性.
- 通过这种催化方法突出了通过这种催化方法访问复杂的性分子的潜力.
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