Simple amino silyl ether organocatalyst for asymmetric hetero Diels–Alder reaction of isatins with enones

Perumalsamy Parasuraman, Divakar Ganesan, Zubeda Begum, Chigusa Seki, Yuko Okuyama, Eunsang Kwon, Koji Uwai, Michio Tokiwa, Suguru Tokiwa, Mitsuhiro Takeshita, Hiroto Nakano

Research output: Contribution to journalArticlepeer-review

Abstract

New two catalysts component system comprising of a primary β-amino silyl ethers as an organocatalyst and N-protected amino acids as a co-catalyst put together worked as an efficient organocatalyst system in the hetero Diels–Alder reaction of isatins with enones affording the chiral spirooxindole-tetrahydropyranones in good chemical yields and stereoselectivities (up to 94%, up to dr 78:22., up to 85% ee).

Original languageEnglish
Pages (from-to)454-464
Number of pages11
JournalChirality
Volume33
Issue number8
DOIs
Publication statusPublished - 2021 Aug

Keywords

  • hetero Diels–Alder reaction
  • organocatalysis
  • spirooxindole
  • β-amino alcohol
  • β-amino silyl ether

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Simple amino silyl ether organocatalyst for asymmetric hetero Diels–Alder reaction of isatins with enones'. Together they form a unique fingerprint.

Cite this