Issue 32, 2012

Comparison of the reactivity of β-thiolactones and β-lactones toward ring-opening by thiols and amines

Abstract

An investigation into the comparative reactivity of simple β-lactones and β-thiolactones toward a thiol and a primary amine is reported. A simple 3-mercaptomethyl-2-oxetanone is found to undergo rearrangement in the presence of aqueous base to give the corresponding thietane-3-carboxylic acid rather than the 3-hydroxymethyl-2-thietanone. Implications for the use of β-thiolactones in bioorganic and medicinal chemistry are discussed.

Graphical abstract: Comparison of the reactivity of β-thiolactones and β-lactones toward ring-opening by thiols and amines

Associated articles

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Article information

Article type
Paper
Submitted
29 Mar 2012
Accepted
14 Jun 2012
First published
14 Jun 2012

Org. Biomol. Chem., 2012,10, 6480-6483

Comparison of the reactivity of β-thiolactones and β-lactones toward ring-opening by thiols and amines

A. Noel, B. Delpech and D. Crich, Org. Biomol. Chem., 2012, 10, 6480 DOI: 10.1039/C2OB25640A

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