Journal
TETRAHEDRON
Volume 74, Issue 42, Pages 6166-6172Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.09.006
Keywords
Enantioselective; Modularly designed organocatalyst; anti-Mannich reaction; Aldehyde; Ketone
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Funding
- Welch Foundation [AX-1593]
- National Science Foundation [CHE 1664278]
- NSF [CHE-1625963]
- National Institute on Minority Health and Health Disparities from the National Institutes of Health [G12MD007591]
- National Institute on Minority Health and Health Disparities [G12MD007591] Funding Source: NIH RePORTER
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A highly stereoselective method for achieving the anti-Mannich reaction of aldehydes and ketones with ethyl (4-methoxyphenylimino)acetate was realized using the modularly designed organocatalysts (MDOs) self-assembled from cinchona alkaloid derivatives and (R)-pyrrolidien-3-carboxylic acid in the reaction media. The desired anti-Mannich products were obtained in good to excellent yields (up to 93%), excellent diastereoselectivities (up to 99:1 dr), and good to high enantioselectivities (up to 99% ee). (C) 2018 Elsevier Ltd. All rights reserved.
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