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A new and high yielding synthesis of unstable pyrroles via a modified Clauson-Kaas reaction.


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Gourlay, BS, Molesworth, PP, Ryan, JH and Smith, JA 2006 , 'A new and high yielding synthesis of unstable pyrroles via a modified Clauson-Kaas reaction.' , Tetrahedron Letters, vol. 47 , pp. 799-801 , doi: 10.1016/j.tetlet.2005.11.104.

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An investigation of the reaction requirements to effect the Clauson-Kaas pyrrole synthesis led to the formulation of a new
procedure that avoids the contact of pyrroles to heat or strongly acidic conditions that cause decomposition of the desired products.
The procedure involves mild hydrolysis of 2,5-dimethoxytetrahydrofuran in water to the activated species 2,5-dihydroxy-
tetrahydrofuran that reacts with primary amines in an acetate buffer at room temperature to give N-substituted pyrroles in high
yield. In the case of chiral amines, pyrrole formation proceeds with no detectable epimerisation. Acid- or heat-sensitive pyrroles
are also obtained in high yield and purity.

Item Type: Article
Authors/Creators:Gourlay, BS and Molesworth, PP and Ryan, JH and Smith, JA
Keywords: Pyrrole Synthesis Clauson-Kaas pyrrolic dimethoxytetrahydrofuran Paul-Knorr
Journal or Publication Title: Tetrahedron Letters
ISSN: 0040-4039
DOI / ID Number: 10.1016/j.tetlet.2005.11.104
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