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A new and high yielding synthesis of unstable pyrroles via a modified Clauson-Kaas reaction
journal contributionposted on 2023-05-16, 18:49 authored by Gourlay, BS, Molesworth, PP, Ryan, JH, Jason SmithJason Smith
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-dihydroxytetrahydrofuran 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. Â© 2005 Elsevier Ltd. All rights reserved.
Publication titleTetrahedron Letters
Department/SchoolSchool of Natural Sciences
Place of publicationOxford