Asymmetric synthesis of atropisomers featuring cyclobutane boronic esters facilitated by ring-strained B-ate complexes.

IF 14.7 1区 综合性期刊 Q1 MULTIDISCIPLINARY SCIENCES
Yu-Wen Sun, Jia-Hui Zhao, Xin-Yu Yan, Chong-Lei Ji, Huangdi Feng, De-Wei Gao
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引用次数: 0

Abstract

The strain-release-driven reactions of bicyclo[1.1.0]butanes (BCBs) have received significant attention from chemists. Notably, 1,2-migratory reactions enabled by BCB-derived B-ate complexes effectively complement the reactions initiated by common BCBs. The desired products are particularly valuable for late-stage transformations due to the presence of the C-B bond. However, asymmetric reactions mediated by BCB-derived boronate complexes have progressed slowly. In this study, we develop an asymmetric synthesis of atropisomers featuring cis-cyclobutane boronic esters facilitated by 1,2-carbon or boron migration of ring-strained B-ate complexes, achieving high enantioselectivity. The reaction is compatible with various aryl, alkenyl, alkyl boronic esters and B2pin2, and shows good compatibility with natural product derivatives. Mechanistic studies are conducted to understand stereoselective control in the dynamic kinetic asymmetric transformations (DYKATs). The target products can undergo a series of transformations, further demonstrating the practicality of this methodology.

环应变b -酸配合物促进环丁烷硼酯的不对称合成。
双环[1.1.0]丁烷(BCBs)的菌株释放驱动反应受到了化学家们的广泛关注。值得注意的是,由bcb衍生的b -酸盐配合物引发的1,2-迁移反应有效地补充了普通bcb引发的反应。由于C-B键的存在,期望的产物对后期转化特别有价值。然而,由bcb衍生的硼酸盐配合物介导的不对称反应进展缓慢。在这项研究中,我们开发了一种不对称合成的以顺式环丁烷硼酯为特征的atropisomers,通过1,2-碳或硼的环应变B-ate配合物迁移,实现了高对映选择性。该反应与各种芳基、烯基、烷基硼酸酯和B2pin2均能相容,并与天然产物衍生物具有良好的相容性。对动力学不对称转化(DYKATs)中的立体选择控制进行了机理研究。目标产品可以经过一系列的转换,进一步证明了该方法的实用性。
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来源期刊
Nature Communications
Nature Communications Biological Science Disciplines-
CiteScore
24.90
自引率
2.40%
发文量
6928
审稿时长
3.7 months
期刊介绍: Nature Communications, an open-access journal, publishes high-quality research spanning all areas of the natural sciences. Papers featured in the journal showcase significant advances relevant to specialists in each respective field. With a 2-year impact factor of 16.6 (2022) and a median time of 8 days from submission to the first editorial decision, Nature Communications is committed to rapid dissemination of research findings. As a multidisciplinary journal, it welcomes contributions from biological, health, physical, chemical, Earth, social, mathematical, applied, and engineering sciences, aiming to highlight important breakthroughs within each domain.
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