A new and high yielding synthesis of unstable pyrroles via a modified Clauson-Kaas reaction
A new and high yielding synthesis of unstable pyrroles via a modified Clauson-Kaas reaction
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DOI：
10.1016/j.tetlet.2005.11.104
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发表时间：
2006-01-30
影响因子：
1.8
通讯作者：
Smith, JA
中科院分区：
文献类型：
--
作者：
Gourlay, BS;Molesworth, PP;Smith, JA
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 beat-sensitive pyrroles are also obtained in high yield and purity. (c) 2005 Elsevier Ltd. All rights reserved.
