Chiral Iodine-Catalyzed Dearomatizative Spirocyclization for the Enantioselective Construction of an All-Carbon Stereogenic Center

Dong-Yang Zhang; Lue Xu; Hua Wu; Liu-Zhu Gong

doi:10.1002/chem.201501583

Chiral Iodine-Catalyzed Dearomatizative Spirocyclization for the Enantioselective Construction of an All-Carbon Stereogenic Center

Chemistry. 2015 Jul 13;21(29):10314-7. doi: 10.1002/chem.201501583. Epub 2015 Jun 10.

Authors

Dong-Yang Zhang¹, Lue Xu¹, Hua Wu¹, Liu-Zhu Gong^{2

3}

Affiliations

¹ Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026 (P. R. China).
² Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026 (P. R. China). gonglz@ustc.edu.cn.
³ Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072 (P. R. China). gonglz@ustc.edu.cn.

PMID: 26095392
DOI: 10.1002/chem.201501583

Abstract

The first enantioselective dearomatizative spirocyclization of 1-hydroxy-N-aryl-2-naphthamide derivatives has been accomplished by chiral organoiodine catalysis to stereoselectively create an all-carbon stereogenic center, providing a straightforward approach to access spirooxindole derivatives in good yields and with high to excellent levels of enantioselectivity. Chiral hypervalent phenyl-λ(3) -iodanes generated in situ from the oxidation of the chiral phenyl iodine actually participate in the asymmetric oxidative dearomatizative spirocyclization reaction.

Keywords: asymmetric catalysis; dearomatization; hypervalent iodine; organocatalysis; spirooxindoles.