The Direct Organocatalytic Asymmetric Mannich Reaction: Unmodified Aldehydes as Nucleophiles

The unprecedented application of unmodified aldehydes as nucleophilic donors in direct catalytic asymmetric Mannich-type reactions is disclosed in a full account. Our efforts in broadening the applicability of chiral pyrrolidine-based catalysts in direct asymmetric Mannich-type reactions led to the...

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Veröffentlicht in:	Journal of organic chemistry 2003-12, Vol.68 (25), p.9624-9634
Hauptverfasser:	Notz, Wolfgang, Tanaka, Fujie, Watanabe, Shin-ichi, Chowdari, Naidu S, Turner, James M, Thayumanavan, Rajeswari, Barbas, Carlos F
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes - chemistry Amino Acids - chemical synthesis Amino Acids - chemistry Amino Alcohols - chemical synthesis Amino Alcohols - chemistry Catalysis Catalytic reactions Chemistry Dioxanes Exact sciences and technology General and physical chemistry Imines - chemistry Lactams - chemical synthesis Lactams - chemistry Mannich Bases - chemistry Models, Chemical Proline - chemistry Pyrrolidines - chemistry Solvents Stereoisomerism Structure-Activity Relationship Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Zusammenfassung:	The unprecedented application of unmodified aldehydes as nucleophilic donors in direct catalytic asymmetric Mannich-type reactions is disclosed in a full account. Our efforts in broadening the applicability of chiral pyrrolidine-based catalysts in direct asymmetric Mannich-type reactions led to the highly diastereo- and enantioselective and concise synthesis of functionalized α- and β-amino acids, β-lactams, and amino alcohols.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo0347359