One Step Selective Counterion Dependent Formation of Conjugated Chiral N-Sulfinylimines from Aldehydes
One Step Selective Counterion Dependent Formation of Conjugated Chiral N-Sulfinylimines from Aldehydes
复制标题
由醛一步选择性依赖反离子形成共轭手性 N-亚磺酰亚胺
DOI：
10.1021/acs.orglett.2c04102
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发表时间：
2023
期刊：
影响因子：
5.2
通讯作者：
Njardarson, Jon T.
中科院分区：
文献类型：
--
作者：
Groch, Jeffrey R.;Lauta, Nicholas R.;Njardarson, Jon T.
本文详细研究了手性N-亚磺酰亚胺膦酸酯试剂的合成及其在醛乙烯基化反应中的应用。两个互补的可扩展的试剂路线，从亚磷酸三烷基酯和甲基膦酸酯，分别提出。这类试剂能够显著简化从醛合成共轭Ellman亚胺的过程，与更经典的基于氧化还原的4步方法相比，现在可以在一个步骤中完成。醛乙烯基化优化已经揭示了显著的协同效应和需要解决以实现高产率的意想不到的竞争反应挑战。
We report a detailed study on the synthesis and aldehyde vinylogation applications of chiral N-sulfinyl imine phosphonate reagents. Two complementary scalable reagent routes, from trialkyl phosphites and methyl phosphonates, respectively, are presented. This reagent class enables significant streamlining in synthesis of conjugated Ellman imines from aldehydes, which can now be accomplished in a single step compared to a more classic 4-step redox-based approach. Aldehyde vinylogation optimizations have revealed significant counterion effects and unexpected competing reaction challenges that needed to be addressed to achieve high yields.