Copper(I)-Catalyzed Conjugate Addition/Enantioselective Protonation with Selenols and α-Substituted α,ß-Unsaturated Thioamides.
Angew Chem Int Ed Engl
; 62(24): e202301422, 2023 Jun 12.
Article
em En
| MEDLINE
| ID: mdl-37085464
ABSTRACT
Herein, a copper(I)-catalyzed asymmetric conjugate addition/protonation with selenols and α-substituted α,ß-unsaturated thioamides is disclosed, which affords a series of chiral selenides in high to excellent enantioselectivity. As for both selenols and α-substituted α,ß-unsaturated thioamides, the reaction enjoys broad substrate scopes. The present catalytic system is also successfully applied to asymmetric selenation of ß-substituted α,ß-unsaturated thioamides. A [Cu-(R,RP )-TANIAPHOS]-SePh species is characterized by its 77 Se NMR spectra, which gives a chemical shift at δ 462â
ppm. Moreover, a {[Cu-(R)-TOL-BINAP]-SePh}2 species is characterized by X-ray analysis, which confirms the formation of Cu-Se bond in the reaction. Finally, the transformations of the thioamide group to amine and thioester are demonstrated to be straightforward.
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MEDLINE
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En
Ano de publicação:
2023
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Article