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

Enantioselective Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds

Enantioselective Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds
Jerome Waser, Durga Prasad Hari
Enantioselective catalytic methods allowing the addition of both a nucleophile and an electrophile onto diazo compounds give a fast access into important building blocks. Herein, we report the highly enantioselective oxyalkynylation of diazo compounds using ethynylbenziodoxol-(on)e reagents and a simple copper bisoxazoline catalyst. The obtained α-benzoyloxy propargylic esters are useful building blocks, which are difficult to synthesize in enantiopure form using other methods. The obtained products could be efficiently transformed into vicinal diols and α-hydroxy propargylic esters without loss in enantiopurity.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b04756

DOI: 10.1021/jacs.7b04756

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