Four-Step One-Pot Catalytic Asymmetric Synthesis of Polysubstituted Tricyclic Compounds: Lipase-Catalyzed Dynamic Kinetic Resolution Followed by an Intramolecular Diels-Alder Reaction

Izuru Tsuchimochi, Shuhei Hori, Yasuo Takeuchi, Masahiro Egi, Tomo O. Satoh, Kyohei Kanomata, Takashi Ikawa, Shuji Akai

Research output: Contribution to journalArticlepeer-review

Abstract

Starting from readily available tertiary alcohols, four different reactions (a 1,3-migration of a hydroxy group, kinetic resolution, racemization, and an intramolecular Diels-Alder reaction) took place under co-catalysis by lipase and oxovanadium compounds in a one-pot process to produce polysubstituted tricyclic carbon frameworks in high yields and with high enantioselectivities. The key to the success of this process was the discovery that a silyl group attached to the terminal carbon of the vinyl moiety completely controls the direction of hydroxy group migration.

Original languageEnglish
JournalSynlett
DOIs
Publication statusAccepted/In press - 2021

Keywords

  • Diels-Alder reaction
  • allylic alcohols
  • asymmetric synthesis
  • dynamic kinetic resolution
  • lipase
  • one-pot reaction

ASJC Scopus subject areas

  • Organic Chemistry

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