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- General Experimental Procedure.To a mixture of solvent (3 mL), dibenzyl azodicarboxylate (90%, 330 mg, 1 mmol),l-proline (23 mg, 0.2 mmol), and propionaldehyde (79 μL, 1.1 mmol) was added acetone (2 mL), and the reaction was stirred at room temperature for 72 h. Then, half-saturated NH4Cl solution and ethyl acetate were added with vigorous stirring; the layers were separated, and the aqueous phase was extracted thoroughly with ethyl acetate. The combined organic phases were dried (Na2SO4), concentrated, and purified by flash column chromatography (silica gel, mixtures of hexanes/ethyl acetate) to afford the desired amino alcohol as a white solid as a mixture of diastereomers.
Dates
| Type | When |
|---|---|
| Created | 22 years, 3 months ago (May 8, 2003, 1:15 a.m.) |
| Deposited | 3 years, 11 months ago (Sept. 21, 2021, 10:40 p.m.) |
| Indexed | 3 months, 3 weeks ago (May 9, 2025, 12:30 p.m.) |
| Issued | 22 years, 4 months ago (April 22, 2003) |
| Published | 22 years, 4 months ago (April 22, 2003) |
| Published Online | 22 years, 4 months ago (April 22, 2003) |
| Published Print | 22 years, 4 months ago (May 1, 2003) |
@article{Chowdari_2003, title={Organocatalytic Asymmetric Assembly Reactions: One-Pot Synthesis of Functionalized β-Amino Alcohols from Aldehydes, Ketones, and Azodicarboxylates}, volume={5}, ISSN={1523-7052}, url={http://dx.doi.org/10.1021/ol034333n}, DOI={10.1021/ol034333n}, number={10}, journal={Organic Letters}, publisher={American Chemical Society (ACS)}, author={Chowdari, Naidu S. and Ramachary, D. B. and Barbas, Carlos F.}, year={2003}, month=apr, pages={1685–1688} }