Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Enantioselective Synthesis of Alkylthioetherpyrrolidine Derivatives via [3+2] Cycloaddition of α-Thioacrylates with Isocyanoacetates

Enantioselective Synthesis of Alkylthioetherpyrrolidine Derivatives via [3+2] Cycloaddition of α-Thioacrylates with Isocyanoacetates
Yun He, Pan-Lin Shao, Qi Wu, Zhi-Peng Wang, Xiao-Jiao Peng, Zi-Rui Li
An unprecedented catalytic asymmetric method for the [3+2] cycloaddition of isocyanoacetates with α-thioacrylates/α-phthalimidoacrylates has been developed with excellent enantioselectivities. The generated pyrrolines could be readily further reduced to an array of structurally various and biologically important pyrrolidine derivatives. α-Tosyloxyacrylate with isocyanoacetates as well as tosylmethylisocyanide could be used to produce 2,4-disubstituted pyrroles.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02266

DOI: 10.1021/acs.joc.7b02266

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