Highly <i>Endo</i>-Selective and Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylide with α-Enones Catalyzed by a Silver(I)/ThioClickFerrophos Complex
Ichiro Oura
Kenta Shimizu
Kenichi Ogata
Shin-ichi Fukuzawa
10.1021/ol100336q.s004
https://acs.figshare.com/articles/journal_contribution/Highly_i_Endo_i_Selective_and_Enantioselective_1_3_Dipolar_Cycloaddition_of_Azomethine_Ylide_with_Enones_Catalyzed_by_a_Silver_I_ThioClickFerrophos_Complex/2776330
A silver(I)/ThioClickFerrophos complex catalyzed the highly <i>endo</i>-selective asymmetric 1,3-dipolar cycloaddition reaction of methyl <i>N</i>-benzylideneglycinate (the source of azomethine ylides) with (<i>E</i>)-acyclic α-enones having an <i>endo</i>/<i>exo</i> ratio of 90/10 to 99/1. The highly functionalized <i>endo</i>-4-acyl pyrrolidines were obtained in good yields with high enantioselectivities (up to 98% ee). The complex also effectively catalyzed <i>endo</i>-selective reactions with 2-cyclopentenone to give the <i>endo</i>-bicyclic pyrrolidine in high enantioselectivity.
2010-04-16 00:00:00
enantioselectivity
Enantioselective
functionalized
ee
Complex
Dipolar
cycloaddition
ratio
source
pyrrolidine
enone
dipolar
Enone
enantioselectivitie
methyl
Azomethine Ylide
Catalyzed
cyclopentenone
yield
endo
azomethine ylides
Cycloaddition