Ambient Temperature Synthesis of High Enantiopurity N-Protected Peptidyl Ketones by Peptidyl Thiol Ester−Boronic Acid Cross-Coupling
- 17 January 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 129 (5), 1132-1140
- https://doi.org/10.1021/ja0658719
Abstract
α-Amino acid thiol esters derived from N-protected mono-, di-, and tripeptides couple with aryl, π-electron-rich heteroaryl, or alkenyl boronic acids in the presence of stoichiometric Cu(I) thiophene-2-carboxylate and catalytic Pd2(dba)3/triethylphosphite to generate the corresponding N-protected peptidyl ketones in good-to-excellent yields and in high enantiopurity. Triethylphosphite plays a key role as a supporting ligand by mitigating an undesired palladium-catalyzed decarbonylation−β-elimination of the α-amino thiol esters. The peptidyl ketone synthesis proceeds at room temperature under nonbasic conditions and demonstrates a high tolerance to functionality.This publication has 40 references indexed in Scilit:
- Phosphine-Free Cross-Coupling Reaction of Arylboronic Acids with Carboxylic Anhydrides or Acyl Chlorides in Aqueous MediaThe Journal of Organic Chemistry, 2006
- “β-cis-SAr effect” on decarbonylation from α,β-unsaturated acyl and aroyl complexesChemical Communications, 2006
- A Unique Catalyst Effects the Rapid Room-Temperature Cross-Coupling of Organozinc Reagents with Carboxylic Acid Fluorides, Chlorides, Anhydrides, and ThioestersJournal of the American Chemical Society, 2004
- Palladium-Catalyzed Synthesis of Aryl Ketones from Boronic Acids and Carboxylic Acids or AnhydridesAngewandte Chemie, 2001
- Structure-based design of ketone-containing, tripeptidyl human rhinovirus 3C protease inhibitorsBioorganic & Medicinal Chemistry Letters, 2000
- Palladium-Catalyzed Cross-Coupling Reactions of Organoboron CompoundsChemical Reviews, 1995
- Coordinating properties of the amide bond. Stability and structure of metal ion complexes of peptides and related ligandsChemical Reviews, 1982
- Simple Method for the Esterification of Carboxylic AcidsAngewandte Chemie, 1978
- The Formation of Linear Polymers from Diene Monomers by a Cyclic Polymerization Mechanism. I. The Structure of Poly-(diallylammonium Halides)1,2Journal of the American Chemical Society, 1958
- Organoboron Compounds. II. The Reducing Action of Some Organoboronic Acids1Journal of the American Chemical Society, 1938