Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Method for Highly Enantioselective Ligation of Two Chiral C(sp3) Stereocenters

Method for Highly Enantioselective Ligation of Two Chiral C(sp3) Stereocenters
E. J. Corey, Eswar Bhimireddy
A method is described for the joining of two α-lithiated C(sp3) stereocenters efficiently and with retention of configuration. The key step involves the effective removal of two electrons from a chiral organocuprate R2CuLi, by i-propyl 2,4-dinitrobenzoate to form a Cu(III) complex that undergoes at −90 °C accelerated reductive elimination enantioselectively and exclusively without the formation of free radicals.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b07366

DOI: 10.1021/jacs.7b07366

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