Thioamide‐Substituted Cinchona Alkaloids as Efficient Organocatalysts for Asymmetric Decarboxylative Reactions of MAHOs
A new class of thioamide‐substituted cinchona derivatives is reported. A convergent and practical approach was developed to insert the thioamide functional group onto the cinchonidine from readily available dithioesters. These organocatalysts were effective in asymmetric decarboxylative Mannich and...
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Veröffentlicht in: | European journal of organic chemistry 2017-08, Vol.2017 (29), p.4319-4323 |
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Sprache: | eng |
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Zusammenfassung: | A new class of thioamide‐substituted cinchona derivatives is reported. A convergent and practical approach was developed to insert the thioamide functional group onto the cinchonidine from readily available dithioesters. These organocatalysts were effective in asymmetric decarboxylative Mannich and protonation reactions of α‐amido‐substituted malonic acid half oxyesters (MAHOs), affording α,β‐ and α‐amino acid derivatives, respectively, in good yields and stereoselectivities.
A new class of thioamide‐substituted cinchona alkaloid derivatives has been successfully synthesized by an efficient approach from easily accessible dithioesters. These organocatalysts were effective in the asymmetric Mannich and enantioselective protonation reactions of α‐amido‐malonic acid half oxyesters (MAHOs) as cheap glycine equivalents to afford α,β‐ and α‐amino acid derivatives, respectively. |
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ISSN: | 1434-193X 1099-0690 |
DOI: | 10.1002/ejoc.201700870 |