13901-77-4Relevant articles and documents
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Hurd,Buess
, p. 5667,5670 (1956)
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Thiazolium-catalyzed additions of acylsilanes: A general strategy for acyl anion addition reactions
Mattson, Anita E.,Bharadwaj, Ashwin R.,Zuhl, Andrea M.,Scheidt, Karl A.
, p. 5715 - 5724 (2007/10/03)
A strategy utilizing N-heterocyclic carbenes (NHCs) derived from thiazolium salts has been developed for the generation of carbonyl anions from acylsilanes. Synthetically useful 1,4-diketones and N-phosphinoyl-α- aminoketones have been prepared in good to excellent yields via NHC-catalyzed additions of acylsilanes to the corresponding α,β-unsaturated systems and N-phosphinoylimines. These organocatalytic reactions are air- and water-tolerant methods to execute robust carbonyl anion addition reactions. Additionally, polysubstituted aromatic furans and pyrroles have been efficiently synthesized in a one-pot process using this carbonyl anion methodology. The addition of alcohols to the reaction renders the process catalytic in thiazolium salt. In an effort to synthesize a potential intermediate along the proposed reaction pathway, silylated thiazolium carbinols have been identified to provide good yields of carbonyl anion addition products when subjected to the standard reaction conditions in the presence of suitable electrophiles.
Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot sila-stetter/paal-knorr strategy
Bharadwaj, Ashwin R.,Scheidt, Karl A.
, p. 2465 - 2468 (2007/10/03)
(Equation Presented) 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.