Issue 80, 2021
From the journal:

Chemical Communications

Rh-Catalyzed cyclization of 2,3-allenoic acids in the presence of 2,3-allenols†‡

Junjie Fan, ORCID logo a   Chunling Fu,a   Xiaoyan Wu ORCID logo *ab  and  Shengming Ma ORCID logo *ab  

* Corresponding authors

a Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, People's Republic of China

b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. China
E-mail: masm@sioc.ac.cn

Abstract

Herein we report a [Cp*RhCl2]2-catalyzed coupling cyclization of two different classes of allenes with 2,3-allenoic acids affording 2(5H)-furanone skeletons of products and 2,3-allenols forming a conjugated (E)-enal or enone functionality to the β-position of the 2(5H)-furanones. These products are important building blocks for the syntheses of potentially bioactive compounds. The reaction proceeded via the nucleometalation, insertion, and stereodefined 1,4-H delivery carried by rhodium.

Graphical abstract: Rh-Catalyzed cyclization of 2,3-allenoic acids in the presence of 2,3-allenols

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Article information

DOI
https://doi.org/10.1039/D1CC04367F
Article type
Communication
Submitted
10 Aug 2021
Accepted
01 Sep 2021
First published
01 Sep 2021

Chem. Commun., 2021,57, 10411-10414

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Rh-Catalyzed cyclization of 2,3-allenoic acids in the presence of 2,3-allenols

J. Fan, C. Fu, X. Wu and S. Ma, Chem. Commun., 2021, 57, 10411 DOI: 10.1039/D1CC04367F

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