Novel aminoimidazole derived proline organocatalysts for aldol reactions

A series of l-proline amides with 2-aminoimidazole have been synthesized and found to be highly efficient organocatalysts for aldol reactions when an appropriate acid was added to control and activate the acceptor carbonyl group. Under optimized reaction conditions, high yields (over 80%) and high s...

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Veröffentlicht in:	Tetrahedron 2012-12, Vol.68 (49), p.10230-10235
Hauptverfasser:	Tang, Gongkun, Gün, Ümit, Altenbach, Hans-Josef
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes Aldol reaction Amides Carbonyl groups Catalysis Catalysts: preparations and properties Chemistry Enantioselectivity Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Imidazole Ketones Organic chemistry Organocatalysis Preparations and properties Proline Selectivity Tetrahedrons Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Beschreibung
Zusammenfassung:	A series of l-proline amides with 2-aminoimidazole have been synthesized and found to be highly efficient organocatalysts for aldol reactions when an appropriate acid was added to control and activate the acceptor carbonyl group. Under optimized reaction conditions, high yields (over 80%) and high selectivities (ee 98%, de 98/2) were obtained in intermolecular aldol reaction even with only 1 equiv of ketone. Likewise, these systems also can catalyze intramolecular aldol reactions with good results. [Display omitted]
ISSN:	0040-4020 1464-5416
DOI:	10.1016/j.tet.2012.09.071