Stereocontrolled α-Allylation of α-Branched N-tert-Butanesulfinyl Ketimines via a Michael–Wittig Cascade for the Construction of Acyclic Quaternary Stereocenters,Organic Letters

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Stereocontrolled α-Allylation of α-Branched N-tert-Butanesulfinyl Ketimines via a Michael–Wittig Cascade for the Construction of Acyclic Quaternary Stereocenters
Organic Letters ( IF 4.9 ) Pub Date : 2022-11-29 , DOI: 10.1021/acs.orglett.2c03801
Chong-Lin Zhu _{1,

2} , Yun Yao ₁ , Chong-Dao Lu ₁

Affiliation

A single-flask cascade of Michael addition and Wittig olefination was developed to allow the stereoselective α-allylic alkylation of α-branched N-tert-butanesulfinyl ketimines for the construction of acyclic quaternary stereocenters bearing two sterically and electronically similar substituents. In this process, tBuOK-promoted stereoselective α-deprotonation gives fully substituted aza-enolates with a stereodefined geometry, Michael addition with α,β-unsaturated phosphonates generates C–C bonds with exceptional stereocontrol, and finally paraformaldehyde trapping of the conjugate addition intermediate generates functionalized α-allylated imines.

中文翻译：

通过 Michael-Wittig 级联对 α-支化 N-叔丁亚磺酰基酮亚胺进行立体控制 α-烯丙基化，用于构建无环四元立构中心

开发了迈克尔加成和维蒂希烯化的单瓶级联，以允许α-支化N-叔丁亚磺酰基酮亚胺的立体选择性α-烯丙基烷基化，用于构建带有两个空间和电子相似取代基的无环四元立构中心。在此过程中， t BuOK 促进的立体选择性 α-去质子化产生具有立体定义几何形状的完全取代的氮杂烯醇化物，与 α,β-不饱和膦酸酯的迈克尔加成生成具有出色立体控制的 C-C 键，最后用多聚甲醛捕获共轭加成中间体生成官能化的α-烯丙基化亚胺。

更新日期：2022-11-29

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