Organocatalytic asymmetric assembly reactions: one-pot synthesis of functionalized beta-amino alcohols from aldehydes,ketones, and azodicarboxylates |
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Authors: | Chowdari Naidu S Ramachary D B Barbas Carlos F |
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Institution: | 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. |
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Abstract: | 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. |
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