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铑催化的环状酮亚胺与炔基氯的[3+2]环加成:一种获得不对称取代和高官能化茚的策略。

Rh-Catalyzed [3+2] Annulation of Cyclic Ketimines and Alkynyl Chloride: A Strategy for Accessing Unsymmetrically Substituted and Highly Functionalizable Indenes.

机构信息

Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction Engineering, School of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei 230009, China.

School of Material Science and Engineering, Hefei University of Technology, Hefei 230009, China.

出版信息

Org Lett. 2022 Dec 23;24(50):9169-9173. doi: 10.1021/acs.orglett.2c02717. Epub 2022 Dec 11.

Abstract

Alkynyl chlorides were found to be extraordinarily novel electrophiles, which could afford a single regioisomer of the [3+2] annulation adducts with cyclic ketimines by rhodium catalysis. The alkenyl chloride moiety in the products provided a valuable functional handle for further diverse transformations. Therefore, this research provided not only a synthetic protocol for accessing unsymmetrically substituted indenyl amines but also a highly divergent solution for decorating the substituting group by postmanipulation of the chloride.

摘要

炔基氯被发现是一种非常新颖的亲电试剂,通过铑催化,能够以单一区域异构体的形式与环状酮亚胺发生[3+2]环加成反应。产物中的烯基氯部分为进一步的多样化转化提供了有价值的功能基。因此,这项研究不仅为获得不对称取代的茚基胺提供了一种合成方案,而且还为通过后处理对氯进行修饰来装饰取代基提供了一种高度多样化的解决方案。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b189/9791992/73bc42477742/ol2c02717_0001.jpg

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