Organocatalytic asymmetric assembly reactions: one-pot synthesis of functionalized beta-amino alcohols from aldehydes, ketones, and azodicarboxylates.
[reaction: see text] l-Proline catalyzed the enzyme-like direct asymmetric assembly of aldehydes, ketones, and azodicarboxylic acid esters to provide optically active beta-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.
Chowdari
Naidu S
NS
The Skaggs Institute for Chemical Biology and the Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Ramachary
D B
DB
Barbas
Carlos F
CF
D000447:Aldehydes / Q000737:chemistry*; D000605:Amino Alcohols / Q000138:chemical synthesis*; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003998:Dicarboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D011392:Proline / Q000737:chemistry; D012997:Solvents; D013237:Stereoisomerism
D000447:Aldehydes; D000605:Amino Alcohols; D001372:Aza Compounds; D003998:Dicarboxylic Acids; D007659:Ketones; D012997:Solvents; D011392:Proline