Muthukumar, Alagesan ; Mamillapalli, N. Chary ; Sekar, Govindasamy (2016) Potassium Phosphate-Catalyzed Chemoselective Reduction of α-Keto Amides: Route to Synthesize Passerini Adducts and 3-Phenyloxindoles Advanced Synthesis & Catalysis, 358 (4). pp. 643-652. ISSN 1615-4150
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Official URL: http://doi.org/10.1002/adsc.201500815
Related URL: http://dx.doi.org/10.1002/adsc.201500815
Abstract
A chemoselective reduction of α‐keto amides to biologically important α‐hydroxy amides (mandelamides) by polymethylhydrosiloxane (PMHS) using 5 mol% potassium phosphate (K3PO4) as catalyst has been developed. This transition metal‐free protocol discloses excellent chemoselectivity for the ketone reduction of α‐keto amides in the presence of other reducible functionalities like ketone, nitro, halides, nitrile and amide. Also, the chemoselectively reduced α‐hydroxy amide has been derivatized to isocyanide‐free Passerini adducts. The N‐alkyl‐α‐hydroxy amides have been successfully converted to 3‐phenyloxindole derivatives by treatment with methanesulfonyl cholride and triethylamine.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to John Wiley and Sons, Inc. |
| ID Code: | 132187 |
| Deposited On: | 14 Dec 2022 09:33 |
| Last Modified: | 14 Dec 2022 09:33 |
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