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A new and high yielding synthesis of unstable pyrroles via a modified Clauson-Kaas reaction.
journal contribution
posted on 2023-05-26, 16:10 authored by Gourlay, BS, Molesworth, PP, Ryan, JH, Jason SmithJason SmithAn 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 LettersVolume
47Pagination
799-801ISSN
0040-4039Publication status
- Published
Rights statement
The definitive version is available at http://www.sciencedirect.com/Repository Status
- Open
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