Direct Access to Highly Enantioenriched α-Branched Acrylonitriles through a Formal Cross Rauhut-Currier Reaction

28 April 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


A highly enantioselective synthesis of α-branched acrylonitriles is reported featuring an unprecedented formal cross Rauhut-Currier reaction consisting of an asymmetric Michael addition/retro-Dieckmann/retro-Michael fragmentation cascade. The method, which involves the use of an acrylonitrile surrogate, is practical, scalable and highly versatile, and provides a straightforward access to a wide range of enantioenriched nitrile-containing building blocks without using acrylonitrile or any source of cyanide. Most importantly, it offers a new tool to incorporate an acrylonitrile moiety in an asymmetric fashion.


Enantioselective Catalysis
Michael Addition
retro-Dieckmann fragmentation
acrylonitrile moiety
Formal Rauhut-Currier reaction

Supplementary materials



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