943319-08-2Relevant academic research and scientific papers
Biology-oriented synthesis of benzopyrano[3,4-c]pyrrolidines
Potowski, Marco,Golz, Christopher,Strohmann, Carsten,Antonchick, Andrey P.,Waldmann, Herbert
supporting information, p. 2895 - 2903 (2015/03/30)
A natural product inspired synthesis of 6,6,5-tricyclic compounds via a silver(I)-catalyzed formal 1,3-dipolar cycloaddition of coumarins with α-iminoesters was developed. The reaction proceeds in a stepwise reaction course under formation of the trans-su
Bis-sulfonyl ethylene as masked acetylene equivalent in catalytic asymmetric [3 + 2] cycloaddition of azomethine ylides
Lopez-Perez, Ana,Adrio, Javier,Carretero, Juan C.
supporting information; experimental part, p. 10084 - 10085 (2009/02/04)
Enantioenriched 3-pyrrolines have been synthesized by highly enantioselective Fesulphos-Cu-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with trans-1,2-bisphenylsulfonyl ethylene, followed by reductive sulfonyl elimination. High levels of reactivity, exoselectivity, and enantioselectivity have been accomplished for a variety of substituted azomethine ylides. This cycloaddition-desulfonylation strategy has been applied as a key step in the enantioselective synthesis of a biologically active C-azanucleoside. Copyright
CuI-Fesulphos complexes: efficient chiral catalysts for asymmetric 1,3-dipolar cycloaddition of azomethine ylides
Cabrera, Silvia,Arrayás, Ramón Gómez,Martín-Matute, Belén,Cossío, Fernando P.,Carretero, Juan C.
, p. 6587 - 6602 (2008/02/05)
The CuI-Fesulphos catalyst system (≤3 mol %) shows an excellent performance in the asymmetric 1,3-dipolar cycloaddition of azomethine ylides. High to very high levels of reactivity, endo/exo selectivity, and enantioselectivity (69->99% ee) are generally achieved with a very wide range of azomethine ylides and dipolarophiles. Based on experimental and computational studies data, a model that accounts for this high enantiocontrol is proposed.
