Expeditious and Chemoselective Synthesis of α-Aryl and α-Alkyl Selenomethylketones via Homologation Chemistry

Org Lett. 2018 May 4;20(9):2685-2688. doi: 10.1021/acs.orglett.8b00896. Epub 2018 Apr 17.

Abstract

Diselenoacetals, previously considered byproducts in homologation tactics en route to α-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 α-aryl- and α-alkyl seleno methylketones through a single chemical operation. No racemization events are observed in the presence of optically pure starting materials.

Publication types

  • Research Support, Non-U.S. Gov't