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A N,N'-dioxide/Mg(OTf)2 complex catalyzed enantioselective α-addition of isocyanides to alkylidene malonates
Weiwei Luo1, Xiao Yuan1, Lili Lin1
1Key Laboratory of Green Chemistry & Technology , Ministry of Education , College of Chemistry , Sichuan University , Chengdu 610064 , China . Email: liuxh@scu.edu.cn ; Email: xmfeng@scu.edu.cn ; ; Tel: +86 28 85418249.
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.