Catalytic Enantioselective α-Allylation of Deconjugated Butenolides with Aza-π-allylpalladium 1,4-Dipoles: Access to Optically Pure 2-Piperidones Bearing an All-Carbon Quaternary Stereocenter

• DOI: 10.1021/acs.orglett.2c03383
• Publication Date: 2022-11-10T13:25:55Z
• Authors: Shu-Pei Yuan; Qing Bao; Ting-Jia Sun; Jian-Qiang Zhao; Zhen-Hua Wang; Yong You; Yan-Ping Zhang; Ming-Qiang Zhou; Wei-Cheng Yuan
• Keywords: Stereocenter; Decarboxylation; Amide

A palladium-catalyzed enantioselective α-allylation of deconjugated butenolides with aza-π-allylpalladium 1,4-diploes, in situ generated from palladium-mediated decarboxylation cyclic carbamates and amide-substituted acyclic carbonates, has been successfully developed. An array enantioenriched 2-piperidones bearing an all-carbon quaternary stereocenter were obtained high yields excellent enantioselectivities (up to 99% yield ee). The utility this method was also showcased by a large-scale reaction synthetic transformations the product.