A new and high yielding synthesis of unstable pyrroles via a modified Clauson-Kaas reaction.
Gourlay, BS and Molesworth, PP and Ryan, JH and Smith, JA (2006) A new and high yielding synthesis of unstable pyrroles via a modified Clauson-Kaas reaction. Tetrahedron Letters, 47 . pp. 799-801. ISSN 0040-4039
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Official URL: http://dx.doi.org/10.1016/j.tetlet.2005.11.104
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.
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|Deposited By:||Dr Jason A Smith|
|Deposited On:||18 Mar 2008 13:47|
|Last Modified:||17 Apr 2009 08:45|
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