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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 11
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Original Articles

Elegant Synthesis of Highly Functionalized 1,2,3-Trisubstituted Cyclopentanes

, &
Pages 1594-1601 | Received 10 Nov 2011, Published online: 06 Mar 2013
 

Abstract

The conversion of cyclic Baylis–Hillman acetates 1 into the corresponding cyano derivatives 2 was achieved using potassium cyanide in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) in aqueous medium. The obtained Michael acceptors 2 easily add primary amines in absolute ethanol to produce a new family of 1,2,3-trisubstituted cyclpentanes 3 in good yields.

GRAPHICAL ABSTRACT

Notes

a Isolated yield after chromatography.

a Isolated yield after chromatography.

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