Asymmetric synthesis of tetrazole and dihydroisoquinoline derivatives by isocyanide-based multicomponent reactions

Qian Xiong, Shunxi Dong, Yushuang Chen, Xiaohua Liu () and Xiaoming Feng ()
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Qian Xiong: Sichuan University
Shunxi Dong: Sichuan University
Yushuang Chen: Sichuan University
Xiaohua Liu: Sichuan University
Xiaoming Feng: Sichuan University

Nature Communications, 2019, vol. 10, issue 1, 1-10

Abstract: Abstract Although isocyanide-based multicomponent reactions were proven to be simple, elegant and facile strategies for the synthesis of highly valuable nitrogen-containing heterocycles, their asymmetric versions accessing to optically active nitrogen heterocyclic compounds are rather limited. Here, we illustrate that, relying on the enantioselective addition of simple isocyanides to C=C bonds, several isocyanide-based multicomponent reactions are realized in the presence of a chiral MgII-N,Nʹ-dioxide catalyst. In the reaction among isocyanide, TMSN3, and alkylidene malonate, three- or four-component reactions could be precisely controlled by modulating reaction conditions, supplying two types of enantioenriched tetrazole-derivatives in moderate to high yields. Possible catalytic cycles via a key zwitterionic intermediate, and the vital roles of H2O or excess ligand are provided based on control experiments. Moreover, taking advantage of this zwitterionic intermediate as a 1,3-dipole, an enantioselective dearomative [3+2] annulation reaction of nonactivated isoquinolines is achieved, furnishing chiral 1,2-dihydroisoquinolines in good to excellent results.

Date: 2019
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DOI: 10.1038/s41467-019-09904-5

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