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Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot sila-Stetter/Paal-Knorr strategy.

Organic letters (2004-07-02)
Ashwin R Bharadwaj, Karl A Scheidt
RESUMEN

[reaction: see text] A multicomponent synthesis of highly substituted pyrroles catalyzed by thiazolium salts has been disclosed. The reaction employs an acyl anion conjugate addition reaction of acylsilanes (sila-Stetter) and unsaturated ketones to generate 1,4-dicarbonyl compounds in situ. The subsequent addition of various amines promotes a Paal-Knorr reaction, affording the desired pyrrole nucleus in an efficient one-pot process.

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(S)-(−)-α-Methylbenzylamine, 98%