Rhodium‐Catalyzed Regioselective C7 <sub>Ar</sub> ‐(Acyl)alkylation of Tryptophan With Allyl Alcohols and Its Late‐Stage Peptide Exemplification
An efficient Rh(III)-catalyzed pivaloyl-directed strategy has been developed for the C7<sub>Ar</sub>-(acyl)alkylation of tryptophans with substituted and unsubstituted allyl alcohols, delivering tryptophan-based unnatural amino acids without compromising their chirality. The disclosed methodology showcased high tolerance of neutral, acidic, and basic amino acids, including Gly, Ala, Val, Leu, Phe, Pro, Asp, Lys, and Thr units, enabling regioselective late-stage functionalization of tryptophan units in a variety of tryptophan-containing dipeptides, tripeptides in reasonable yields.
Authors
- Siva Sankar Panda (ORCID: https://orcid.org/0000-0003-3668-104X)
- Somnath Arjun Borade
- Rajeev Sakhuja (ORCID: https://orcid.org/0000-0002-9284-9137)
- Kiran Bajaj (ORCID: https://orcid.org/0000-0003-4483-4747)
- Disha Tank
- Mukul Yadav (ORCID: https://orcid.org/0000-0002-0752-7847)
Institutions
- University of Delhi (IN)
- Amity University (IN)
- Augusta University (US)
- Augusta University Health (US)
- Birla Institute of Technology and Science, Pilani (IN)
Publication Details
- Journal
- Chemistry - An Asian Journal
- Published
- 2025-12-01
- DOI
- https://doi.org/10.1002/asia.70475
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.00