Organocatalytic Asymmetric Assembly Reactions:  One-Pot Synthesis of Functionalized β-Amino Alcohols from Aldehydes, Ketones, and Azodicarboxylates

• Published in: Organic letters Vol. 5; no. 10; pp. 1685 - 1688
• Main Authors: Chowdari, Naidu S, Ramachary, D. B, Barbas, Carlos F
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 15.05.2003; Amer Chemical Soc
• Subjects: Aldehydes - chemistry; Amino Alcohols - chemical synthesis; Aza Compounds - chemical synthesis; Aza Compounds - chemistry; Catalysis; Chemistry; Chemistry, Organic; Dicarboxylic Acids - chemical synthesis; Dicarboxylic Acids - chemistry; Ketones - chemistry; Models, Molecular; Molecular Conformation; Physical Sciences; Proline - chemistry; Science & Technology; Solvents; Stereoisomerism; ROUTE; ALPHA-AMINO; AMINATION; DIELS-ALDER REACTIONS; ALPHA,BETA-UNSATURATED KETONES; ALDOL REACTIONS; CATALYST; MICHAEL ADDITIONS
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol034333n

l-Proline catalyzed the enzyme-like direct asymmetric assembly of aldehydes, ketones, and azodicarboxylic acid esters to provide optically active β-amino alcohols. This assembly reaction uses both aldehydes and ketones as donors in one pot. The aldol-derived stereocenter is formed with a reduced facial selectivity in reactions involving (R)-amino aldehydes. The reactions can be performed on a multigram scale under operationally simple and safe conditions without the requirement of an inert atmosphere or dry solvents.