Organocatalytic Allylic Alkylation of α-(Alkylideneamino)nitriles and Its Application in the Preparation of Multisubstituted 1-Pyrrolines

Lang Zhao; Yan Yan; Zhong-Lin Wei; Wei-Wei Liao

doi:10.1021/acs.joc.2c01072

Organocatalytic Allylic Alkylation of α-(Alkylideneamino)nitriles and Its Application in the Preparation of Multisubstituted 1-Pyrrolines

J Org Chem. 2022 Aug 5;87(15):10090-10104. doi: 10.1021/acs.joc.2c01072. Epub 2022 Jul 11.

Authors

Lang Zhao¹, Yan Yan², Zhong-Lin Wei¹, Wei-Wei Liao¹

Affiliations

¹ Department of Organic Chemistry, College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. China.
² State Key Lab of Inorganic Synthesis and Preparative Chemistry, Jilin University, Changchun 130012, P. R. China.

PMID: 35816383
DOI: 10.1021/acs.joc.2c01072

Abstract

A synthetic approach for the construction of functionalized diverse 1-pyrrolines incorporating β-quaternary carbon centers under mild reaction conditions has been reported, in which α-allyl α-(alkylideneamino)nitriles generated from a Lewis base-catalyzed allylic alkylation reaction engaged in a Lewis base-mediated tandem intramolecular cyclization to deliver the targeted molecules in a catalytically atom-economic fashion.