Issue 18, 2012
From the journal:

Organic & Biomolecular Chemistry

Chemoselective synthesis of highly substituted 1,2-allenyl ketones, furans, and 2-alkynyl ketones from reaction of lithium selenolates with 1-(1-alkynyl)cyclopropyl ketones and electrophiles†

Jianfeng Xu,a   Shugao Zhu,a   Luling Wu*a  and  Xian Huang‡a  

* Corresponding authors

a Department of Chemistry, Zhejiang University (Xixi Campus), Hangzhou, Zhejiang, P.R. China
E-mail: wululing@zju.edu.cn
Fax: (+86) 571-88807077

Abstract

A homo-Michael addition reaction of lithium selenolates with 1-(1-alkynyl)cyclopropyl ketones and the subsequent reaction with electrophiles such as PhSeBr, NFSI and NCS is reported. Based on the nature of electrophiles, this reaction may afford highly substituted 1,2-allenyl ketones or furans (E+ = PhSe+) and 2-alkynyl ketones (E+ = F+, Cl+, active halides) as the final products, respectively.

Graphical abstract: Chemoselective synthesis of highly substituted 1,2-allenyl ketones, furans, and 2-alkynyl ketones from reaction of lithium selenolates with 1-(1-alkynyl)cyclopropyl ketones and electrophiles

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Article information

DOI
https://doi.org/10.1039/C2OB25071C
Article type
Paper
Submitted
11 Jan 2012
Accepted
14 Mar 2012
First published
15 Mar 2012

Org. Biomol. Chem., 2012,10, 3705-3714

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Chemoselective synthesis of highly substituted 1,2-allenyl ketones, furans, and 2-alkynyl ketones from reaction of lithium selenolates with 1-(1-alkynyl)cyclopropyl ketones and electrophiles

J. Xu, S. Zhu, L. Wu and X. Huang, Org. Biomol. Chem., 2012, 10, 3705 DOI: 10.1039/C2OB25071C

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