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

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posted on 2023-05-26, 16:10 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-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.

History

Publication title

Tetrahedron Letters

Volume

47

Pagination

799-801

ISSN

0040-4039

Publication status

  • Published

Rights statement

The definitive version is available at http://www.sciencedirect.com/

Repository Status

  • Open

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