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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 20
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Original Articles

Method for Regio- and Stereoselective Synthesis of (E)-β,γ-Unsaturated Acids from Aldehydes Under Solvent-Free Conditions

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Pages 3093-3100 | Received 11 May 2009, Published online: 13 Sep 2010
 

Abstract

Synthesis of (E)-β,γ-unsaturated acids from aldehydes with malonic acid has been explored under solvent-free conditions. The modified Knoevenagel condensation reaction with N-methyl morpholine (NMM) as catalyst exhibits highly β,γ-regioselectivity and exclusively E-stereoselectivity. A mechanism accounting for both regio- and stereoselectivity has been proposed and preliminarily studied.

Notes

a Yields refer to isolated combined product of β,γ- and α,β-hexenoic acids.

b Determined by 1H NMR analysis of the crude product.

c Ratio of E:Z refers to β,γ-hexenoic acids, and >99:1 means only one isomer was observed.

a Yields refer to isolated combined product of β,γ- and α,β-unsaturated acids.

b Determined by 1H NMR analysis of the crude product.

c Ratio of E:Z refers to β,γ-unsaturated acids, and >99:1 means only one isomer was observed.

d Data in parantheses refer to the results of reaction with Et3N instead of NMM.

a Yields refer to isolated combined product of β,γ- and α,β-isomers.

b Determined by 1H NMR analysis of crude product.

c Ratio of E:Z refers to β,γ-isomers, and >99:1 means only one isomer was observed.

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