A N ,N '-dioxide/Mg(OTf)2 complex catalyzed enantioselective α-addition of isocyanides to alkylidene malonates

Chemical Science
Weiwei LuoXiaoming Feng

Abstract

A highly efficient catalytic asymmetric α-addition of isocyanides to alkylidene malonates was accomplished. The process was based on the utilization of a chiral N,N'-dioxide/MgII catalyst, delivering a variety of 2-alkyl-5-aminooxazoles in up to 99% yield and 96% ee under mild reaction conditions. Besides, a chiral imide and dipeptide could be easily obtained by ring-opening of the oxazole product, both of which are important structural motifs for many biologically active compounds. Based on the experimental investigations and previous work, a possible transition state model was proposed.

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Citations

Aug 7, 2020·Organic & Biomolecular Chemistry·Ying SunBo Liu
May 18, 2017·Organic & Biomolecular Chemistry·Hélène Pellissier
Feb 20, 2018·Chemistry : a European Journal·Jingchuan ZhangXiaoming Feng
Feb 25, 2021·The Journal of Organic Chemistry·Ivor SmajlagicTravis Dudding

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