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Organocatalytic asymmetric assembly reactions: one-pot synthesis of functionalized beta-amino alcohols from aldehydes, ketones, and azodicarboxylates. 2003

Naidu S Chowdari, and D B Ramachary, and Carlos F Barbas
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.

[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.

UI MeSH Term Description Entries
D007659 Ketones Organic compounds containing a carbonyl group Ketone
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D011392 Proline A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons. L-Proline,L Proline
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D003998 Dicarboxylic Acids Acyclic acids that contain two carboxyl groups and have the formula HO2C-R-CO2H, where R may be an aromatic or aliphatic group. Acids, Dicarboxylic
D000447 Aldehydes Organic compounds containing a carbonyl group in the form -CHO. Aldehyde
D000605 Amino Alcohols Compounds possessing both a hydroxyl (-OH) and an amino group (-NH2). Alcohols, Amino
D001372 Aza Compounds Organic chemicals where carbon atoms have been replaced by nitrogen atoms. Compounds, Aza
D012997 Solvents Liquids that dissolve other substances (solutes), generally solids, without any change in chemical composition, as, water containing sugar. (Grant & Hackh's Chemical Dictionary, 5th ed) Solvent

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