4.3 Article

Synthesis of Enantiopure Benzo Fused Cyclic Sulfoximines Through Stereoselective [3+2] Cycloaddition between N-tert-Butanesulfinyl [(2-Pyridyl)sulfonyl]-difluoromethyl Ketimines and Arynes

Journal

HELVETICA CHIMICA ACTA
Volume 104, Issue 4, Pages -

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/hlca.202100019

Keywords

arynes; cycloaddition; fluorine; N-tert-butanesulfinyl imine; sulfoximines

Funding

  1. National Basic Research Program of China (973 Program) [2016YFB0101200]
  2. National Natural Science Foundation of China [21632009]
  3. Key Programs of the Chinese Academy of Sciences [KGZD-EW-T08]
  4. Key Research Program of Frontier Sciences of CAS [QYZDJ-SSW-SLH049]
  5. Shanghai Science and Technology Program [18JC1410601]
  6. Syngenta Ph.D. Studentship

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The stereoselective [3+2] cycloaddition reaction between N-tert-butanesulfinyl ketimines and arynes has been successfully extended to the synthesis of enantiopure [(2-pyridyl)sulfonyl]difluoromethylated cyclic sulfoximines. The use of 2-PySO2CF2 as a facilitating group has opened up new opportunities for further research due to the diverse relativity of 2-pyridyl sulfones.
The previously developed stereoselective [3+2] cycloaddition between N-tert-butanesulfinyl ketimines and arynes has been extended to the synthesis of enantiopure [(2-pyridyl)sulfonyl]difluoromethylated cyclic sulfoximines. The use of 2-PySO2CF2 as the facilitating group offers new opportunities for the elaboration of the [3+2] cycloaddition products by virtue of the diverse relativity of 2-pyridyl sulfones.

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