Organocatalytic enantioselective Michael addition of cyclic hemiacetals to nitroolefins: A facile access to chiral substituted 5- and 6-membered cyclic ethers

Yadong Zhu, Pengfei Qian, Jiyang Yang, Shaohua Chen, Yanwei Hu, Ping Wu, Wei Wang, Wei Zhang, Shilei Zhang

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

An efficient aminocatalytic enantioselective Michael addition of readily available cyclic hemiacetals to nitroolefins has been developed. The strategy serves as a powerful approach to synthetically valuable chiral 3-substituted tetrahydrofurans (THFs) and tetrahydropyrans (THPs). The synthetic utilities of the versatile Michael adducts also have been demonstrated in the synthesis of 2,3-disubstituted cyclic ethers, α-substituted lactones and venlafaxine analogues.

Original languageEnglish (US)
Pages (from-to)4769-4775
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number16
DOIs
StatePublished - Apr 28 2015
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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