A copper-catalyzed, pH-neutral construction of high-enantiopurity peptidyl ketones from peptidic s-acylthiosalicylamides in air at room temperature.
A copper-catalyzed transformation of peptidic thiol esters and boronic acids gives peptidyl ketones and takes place in DMF or DMF/H(2)O at room temperature in air (see scheme). This aerobic reaction only occurs at a thiol ester group capable of coordinating to Cu through its appendage on the sulfur center and is not hampered by racemization of the reactants or products.
Liebeskind
Lanny S
LS
Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, GA 30322, USA. chemLL1@emory.edu
Yang
Hao
H
Li
Hao
H
D000388:Air; D000577:Amides / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D010455:Peptides / Q000737:chemistry*; D012457:Salicylamides / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature
D000577:Amides; D007659:Ketones; D010455:Peptides; D012457:Salicylamides; D003300:Copper