Enantioselective Olefin Hydrocyanation Without Cyanide

23 October 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


The enantioselective hydrocyanation of olefins represents a conceptually straightforward approach to prepare enantiomerically enriched nitriles. These, in turn, comprise or are intermediates in the synthesis of many pharmaceuticals and their synthetic derivatives. Herein, we report a cyanide-free dual Pd/CuH-catalyzed protocol for the asymmetric Markovnikov hydrocyanation of vinyl arenes and the anti-Markovnikov hydrocyanation of terminal olefins in which oxazoles function as nitrile equivalents. After an initial hydroarylation process, the oxazole substructure was deconstructed using a [4+2]/retro-[4+2] sequence to afford the enantioenriched nitrile product under mild reaction conditions.


Asymmetric Catalysis
Copper Hydride
Dual Catalysis

Supplementary materials

Supporting information


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