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.
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.
Naidu S
NS
Chowdari
D B
DB
Ramachary
Carlos F
CF
Barbas
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