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

ABSTRACT: A highly efficient catalytic asymmetric ?-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.

SUBMITTER: Luo W

PROVIDER: S-EPMC6016448 | biostudies-other | 2016 Jul

REPOSITORIES: biostudies-other

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

Luo Weiwei W Yuan Xiao X Lin Lili L Zhou Pengfei P Liu Xiaohua X Feng Xiaoming X

Chemical science 20160422 7

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 activ ...[more]

PMID: 30155124

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