Diselenoacetals, previously considered byproducts in homologation tactics en route to alpha-selenoketones, are herein found to be excellent starting materials for this purpose. The easy selenium/lithium exchange they undergo affords seleno carbanions which are smoothly added to Weinreb amides to chemoselectively prepare alpha-aryl- and alpha-alkyl seleno methylketones through a single chemical operation. No racemization events are observed in the presence of optically pure starting materials.
Expeditious and Chemoselective Synthesis of α-Aryl and α-Alkyl Selenomethylketones via Homologation Chemistry / Senatore, Raffaele; Castoldi, Laura; Ielo, Laura; Holzer, Wolfgang; Pace, Vittorio. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 20:9(2018), pp. 2685-2688. [10.1021/acs.orglett.8b00896]
Expeditious and Chemoselective Synthesis of α-Aryl and α-Alkyl Selenomethylketones via Homologation Chemistry
Pace, Vittorio
2018
Abstract
Diselenoacetals, previously considered byproducts in homologation tactics en route to alpha-selenoketones, are herein found to be excellent starting materials for this purpose. The easy selenium/lithium exchange they undergo affords seleno carbanions which are smoothly added to Weinreb amides to chemoselectively prepare alpha-aryl- and alpha-alkyl seleno methylketones through a single chemical operation. No racemization events are observed in the presence of optically pure starting materials.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
