Asymmetric Synthesis of Chiral Dihydrothiopyrans via an Organocatalytic Enantioselective Formal Thio [3 + 3] Cycloaddition Reaction with Binucleophilic Bisketone Thioethers Journal Articles uri icon

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abstract

  • An unprecedented organocatalytic highly enantioselective approach to a 3,4-dihydro-2H-thiopyran scaffold with two contiguous stereogenic centers has been implemented through a formal thio [3 + 3] cycloaddition process involving a Michael-aldol condensation cascade sequence. Notably, a new class of binucleophilic bisketone thioethers is designed for the process. Furthermore, the fine-tuning of their reactivity enables the cascade process to proceed with highly regioselectively.

authors

  • Wang, Shengzheng
  • Zhang, Yongqiang
  • Dong, Guoqiang
  • Wu, Shanchao
  • Zhu, Shiping
  • Miao, Zhenyuan
  • Yao, Jianzhong
  • Li, Hao
  • Li, Jian
  • Zhang, Wannian
  • Sheng, Chunquan
  • Wang, Wei

publication date

  • November 1, 2013