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使用新型手性Yb(OTf)-pybox配合物实现未保护吲哚与硝基烯烃的催化不对称傅克烷基化反应。

Catalytic asymmetric Friedel-Crafts alkylation of unprotected indoles with nitroalkenes using a novel chiral Yb(OTf)-pybox complex.

作者信息

Karimi Babak, Jafari Ehsan, Mansouri Fariborz, Tavakolian Mina

机构信息

Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), Prof. Sobouti Boulevard, PO-Box 45195-1159, Zanjan, 45137-66731, Iran.

Research Center for Basic Sciences & Modern Technologies (RBST), Institute for Advanced Studies in Basic Sciences (IASBS), Prof. Sobouti Boulevard, Zanjan, 45137-66731, Iran.

出版信息

Sci Rep. 2023 Sep 7;13(1):14736. doi: 10.1038/s41598-023-41921-9.

Abstract

Chiral chloro-indeno pybox has served as a new ligand for the Yb(OTf)-catalyzed asymmetric Friedel-Crafts alkylation reaction of indoles with nitroalkenes. The tunable nature of pybox ligands enables the rational design of catalysts for optimal performance in terms of both activity and stereoselectivity in a Friedel-Crafts-type reaction. Good to excellent yields and enantioselectivities were obtained for a relatively wide range of substrates, including sterically hindered compounds, under optimized reaction conditions.

摘要

手性氯代茚并吡唑啉酮已作为一种新型配体,用于Yb(OTf)催化的吲哚与硝基烯烃的不对称傅克烷基化反应。吡唑啉酮配体的可调性使得能够合理设计催化剂,以在傅克型反应的活性和立体选择性方面实现最佳性能。在优化的反应条件下,对于包括空间位阻化合物在内的相对广泛的底物,获得了良好至优异的产率和对映选择性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cde8/10484919/d17eeae7ab09/41598_2023_41921_Sch1_HTML.jpg

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