Issue 45, 2012
From the journal:

Organic & Biomolecular Chemistry

Tandem allylic substitution–5-exo-dig-carbocyclization: a [4 + 1]-annulation approach to arylidene cyclopentenes from MBH-acetates of acetylenic aldehydes†

Chada Raji Reddy,*a   Paridala Kumaraswamya  and  Motatipally Damoder Reddya  

* Corresponding authors

a Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India
E-mail: rajireddy@iict.res.in
Fax: +91-40-27160512

Abstract

A new entry for the synthesis of functionalized arylidene cyclopentenes under metal-free reaction conditions is disclosed via the base-promoted [4 + 1]-annulation of Morita–Baylis–Hillman acetates of acetylenic aldehydes with active methylene derivatives involving tandem allylic substitution followed by 5-exo-dig-carbocyclization.

Graphical abstract: Tandem allylic substitution–5-exo-dig-carbocyclization: a [4 + 1]-annulation approach to arylidene cyclopentenes from MBH-acetates of acetylenic aldehydes

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Article information

DOI
https://doi.org/10.1039/C2OB26934A
Article type
Paper
Submitted
02 Oct 2012
Accepted
08 Oct 2012
First published
09 Oct 2012

Org. Biomol. Chem., 2012,10, 9052-9057

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Tandem allylic substitution–5-exo-dig-carbocyclization: a [4 + 1]-annulation approach to arylidene cyclopentenes from MBH-acetates of acetylenic aldehydes

C. R. Reddy, P. Kumaraswamy and M. D. Reddy, Org. Biomol. Chem., 2012, 10, 9052 DOI: 10.1039/C2OB26934A

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