Issue 10, 2020
From the journal:

Chemical Science

Catalytic enantioselective arylative cyclizations of alkynyl 1,3-diketones by 1,4-rhodium(i) migration†

Alistair Groves,ab   Jinwei Sun,abc   Hal R. I. Parke,ab   Michael Callingham,ab   Stephen P. Argent,‡b   Laurence J. Taylor‡b  and  Hon Wai Lam ORCID logo *ab  

* Corresponding authors

a The GlaxoSmithKline Carbon Neutral Laboratories for Sustainable Chemistry, University of Nottingham, Jubilee Campus, Triumph Road, Nottingham, UK
E-mail: hon.lam@nottingham.ac.uk

b School of Chemistry, University of Nottingham, University Park, Nottingham, UK

c Jiangsu Collaborative Innovation Center of Atmospheric Environment and Equipment Technology, Jiangsu Key Laboratory of Atmospheric Environment Monitoring and Pollution Control, School of Chemistry and Materials Science, Nanjing University of Information Science and Technology, Nanjing, Jiangsu 210044, China

Abstract

The enantioselective synthesis of densely functionalized polycarbocycles by the rhodium(I)-catalyzed reaction of arylboronic acids with 1,3-diketones is described. The key step in these desymmetrizing domino addition–cyclization reactions is an alkenyl-to-aryl 1,4-Rh(I) migration, which enables arylboronic acids to function effectively as 1,2-dimetalloarene surrogates.

Graphical abstract: Catalytic enantioselective arylative cyclizations of alkynyl 1,3-diketones by 1,4-rhodium(i) migration

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Article information

DOI
https://doi.org/10.1039/C9SC06309A
Article type
Edge Article
Submitted
12 Dec 2019
Accepted
05 Feb 2020
First published
06 Feb 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2020,11, 2759-2764

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Catalytic enantioselective arylative cyclizations of alkynyl 1,3-diketones by 1,4-rhodium(I) migration

A. Groves, J. Sun, H. R. I. Parke, M. Callingham, S. P. Argent, L. J. Taylor and H. W. Lam, Chem. Sci., 2020, 11, 2759 DOI: 10.1039/C9SC06309A

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