2023
DOI: 10.1002/ejoc.202301010
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Cross‐Linked Pseudopeptides via Pd‐Catalyzed Carbonylative Coupling of α‐Amino Acid Iodides with α‐Amino Acid Esters in the Presence of a CO Surrogate

Gajanan K. Rathod,
Rahul Jain

Abstract: We report synthesis of cross‐linked pseudopeptides via palladium‐catalyzed carbonylative cross‐coupling reaction. The reaction involves the coupling of α‐amino acid iodides with α‐amino acid esters via in situ CO insertion to give pseudopeptides linked by way of the side chain of the electrophilic counterpart. The key features are the use of sustainable in situ CO surrogate, simple non‐inert conditions, short time, and substrate scope. Both amino acids and peptide iodides were utilized as coupling partners.

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“…The products were highly enantioselective and formed at milder conditions of 80 °C in 35 min. They were the first to explain the regioselectivity of histidine [141] …”
Section: Microwave‐assisted Carbonylationsmentioning
confidence: 99%
“…The products were highly enantioselective and formed at milder conditions of 80 °C in 35 min. They were the first to explain the regioselectivity of histidine [141] …”
Section: Microwave‐assisted Carbonylationsmentioning
confidence: 99%