Cooperative copper-squaramide catalysis for the enantioselective N–H insertion reaction with sulfoxonium ylides |
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Authors: | Lucas G. Furniel,Radell Echemendí a,Antonio C. B. Burtoloso |
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Affiliation: | São Carlos Institute of Chemistry, University of São Paulo, São Carlos, SP CEP 13560-970 Brazil, |
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Abstract: | The first examples of a highly efficient and enantioselective carbene-mediated insertion reaction, from a sulfur ylide, are described. By way of a catalytic asymmetric insertion reaction into N–H bonds from carbonyl sulfoxonium ylides and anilines, using a copper-bifunctional squaramide cooperative catalysis approach, thirty-seven α-arylglycine esters were synthesized in enantiomeric ratios up to 92 : 8 (99 : 1 after a single recrystallization) and reaction yields ranging between 49–96%. Furthermore, the protocol benefits from quick reaction times and is conducted in a straightforward manner.The first examples of a highly efficient and enantioselective carbene-mediated insertion reaction, from a sulfur ylide, are described. |
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