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
Ielo, Laura;Pace, Vittorio
Last
2018-01-01
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.
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