Lucas G. Furniel, Radell Echemendía and Antonio C. B. Burtoloso
Chem. Sci., 2021,12, 7453-7459
DOI:
10.1039/D1SC00979F,
Edge Article
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.