Picolinamides and Iodoalkynes Enable Palladium-Catalyzed syn-Aminoalkynylation of Di- and Trisubstituted Alkenes to Give Pyrrolidines
Abstract
Palladium-catalyzed aminoalkynylation of electronically unbiased olefins with iodoalkynes is reported. The picolinamide auxiliary enables for the first time the syn-selective aminoalkynylation of mono-, di- and trisubstituted alkenes to afford the corresponding pyrrolidines in up to 97 % yield and as single diastereomers. Furthermore, through a C-H activation approach, the picolinamide allows the rapid synthesis of functionalized olefins, which are suitable cyclization precursors. Facile and orthogonal deprotection of the amides and (SiPr3)-Pr-i-acetylenes in the products, and a subsequent Pictet-Spengler reaction is demonstrated. Mehr anzeigen
Persistenter Link
https://doi.org/10.3929/ethz-b-000549161Publikationsstatus
publishedExterne Links
Zeitschrift / Serie
Angewandte Chemie. International EditionBand
Seiten / Artikelnummer
Verlag
Wiley-VCHThema
Alkenes; Alkynes; C-C Coupling; Nitrogen Heterocycles; Pd CatalysisOrganisationseinheit
03511 - Carreira, Erick M. / Carreira, Erick M.