Issue 25, 2016
From the journal:

Organic & Biomolecular Chemistry

Rh-catalysed [5 + 1] cycloaddition of allenylcyclopropanes and CO: reaction development and application to the formal synthesis of (−)-galanthamine†

Cheng-Hang Liua  and  Zhi-Xiang Yu*a  

* Corresponding authors

a Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China
E-mail: yuzx@pku.edu.cn

Abstract

A Rh-catalysed [5 + 1] cycloaddition of allenylcyclopropanes and CO has been developed to synthesize functionalized 2-methylidene-3,4-cyclohexenones. The scope of this methodology has been investigated, showing that various functional groups can be tolerated. Both di- and tri-substituted allenylcyclopropanes can be applied to this cycloaddition and the [5 + 1] cycloadducts with the E configuration were obtained as the major products. In addition, the present [5 + 1] cycloaddition reaction has been utilized as a key step in the formal synthesis of the natural product (−)-galanthamine.

Graphical abstract: Rh-catalysed [5 + 1] cycloaddition of allenylcyclopropanes and CO: reaction development and application to the formal synthesis of (−)-galanthamine

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Article information

DOI
https://doi.org/10.1039/C6OB00660D
Article type
Communication
Submitted
28 Mar 2016
Accepted
13 May 2016
First published
17 May 2016

Org. Biomol. Chem., 2016,14, 5945-5950

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Rh-catalysed [5 + 1] cycloaddition of allenylcyclopropanes and CO: reaction development and application to the formal synthesis of (−)-galanthamine

C. Liu and Z. Yu, Org. Biomol. Chem., 2016, 14, 5945 DOI: 10.1039/C6OB00660D

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