Simplifying the Synthesis of Nonproteinogenic Amino Acids via Palladium-Catalyzed δ-Methyl C-H Olefination of Aliphatic Amines and Amino Acids.
| Autor: | Bhattacharya T; Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India., Baroliya PK; Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.; Department of Chemistry, Mohanlal Sukhadia University, Udaipur 313001, India., Al-Thabaiti SA; Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia., Maiti D; Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India. |
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| Jazyk: | angličtina |
| Zdroj: | JACS Au [JACS Au] 2023 Jun 22; Vol. 3 (7), pp. 1975-1983. Date of Electronic Publication: 2023 Jun 22 (Print Publication: 2023). |
| DOI: | 10.1021/jacsau.3c00215 |
| Abstrakt: | Transition metal-catalyzed directing group assisted C-H functionalizations provide a straightforward access to a wide variety of nonproteinogenic amino acids. While altering the side chain of an existing natural amino acids is one way, introducing a functional group to an aliphatic amine to synthesize versatile unnatural amino acids is another exciting avenue. In this work, we explore both the possibilities by the palladium-catalyzed δ -C( sp 3 )-H olefination of aliphatic amines and amino acids. A diverse substrate scope including sequential difunctionalizations followed by post synthetic transformations were achieved to understand the applicability of the current protocol. An in-depth mechanistic study was carried out to learn the mode of the reaction pathway. Competing Interests: The authors declare no competing financial interest. (© 2023 The Authors. Published by American Chemical Society.) |
| Databáze: | MEDLINE |
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