Asymmetric synthesis of chiral dihydrothiopyrans via an organocatalytic enantioselective formal thio [3 + 3] cycloaddition reaction with binucleophilic bisketone thioethers

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

Research output: Contribution to journalArticlepeer-review

28 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)5570-5573
Number of pages4
JournalOrganic Letters
Volume15
Issue number21
DOIs
StatePublished - Nov 1 2013
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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