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涉及环状二芳基碘鎓盐的含多个手性元素的联芳基亚磺酰亚胺的不对称合成。

Asymmetric Synthesis of Biaryl Sulfilimines Bearing Multiple Chiral Elements Involving Cyclic Diaryliodoniums.

作者信息

Liu Xiangyu, Ye Zenghui, Liu Jici, Wu Yanqi, Zhang Fengzhi

机构信息

School of Pharmacy, Hangzhou Medical College, Hangzhou 310000, China.

School of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, China.

出版信息

Org Lett. 2025 Jun 27;27(25):6695-6701. doi: 10.1021/acs.orglett.5c01776. Epub 2025 Jun 11.

Abstract

The enantio- and diastereoselective synthesis of biaryl atropisomers with a sulfur stereogenic center is a significant challenge for current chemical synthesis due to the lack of effective synthetic strategies. Herein, we report an efficient method for the construction of chiral biaryl sulfilimines possessing both axial and sulfur central chiralities via copper/chiral cobalt anion-catalyzed sulfuration of cyclic diaryliodoniums under mild conditions. Various axial chiral biaryl sulfilimines were efficiently prepared in high yields (up to 99%) and enantioselectivities (up to 98% ee), which can be easily transformed into a wide range of valuable chiral biaryl sulfoximines and their derivatives.

摘要

由于缺乏有效的合成策略,对于当前化学合成而言,构建具有硫立体中心的联芳基阻转异构体的对映选择性和非对映选择性合成是一项重大挑战。在此,我们报道了一种在温和条件下通过铜/手性钴阴离子催化环状二芳基碘鎓盐的硫化反应来构建同时具有轴向和硫中心手性的手性联芳基亚砜亚胺的有效方法。各种轴向手性联芳基亚砜亚胺能够以高产率(高达99%)和对映选择性(高达98% ee)高效制备,并且可以很容易地转化为多种有价值的手性联芳基亚砜亚胺及其衍生物。

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