Regioselective Synthesis of α-Functional Stilbenes via Precise Control of Rapid cis- trans Isomerization in Flow

Hyune Jea Lee, Yuya Yonekura, Nayoung Kim, Jun Ichi Yoshida, Heejin Kim

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

The rapid cis-trans isomerization of α-anionic stilbene was regioselectively controlled by using flow microreactors, and its reaction with various electrophiles was conducted. The reaction time was precisely controlled within milliseconds to seconds at -50 °C to selectively give the cis- or trans-isomer in high yields. This synthetic method in flow was well-applied to synthesize precursors of commercial drug compound, (E)- and (Z)-tamoxifen with high regioselectivity and productivity.

Original languageEnglish
Pages (from-to)2904-2910
Number of pages7
JournalOrganic Letters
Volume23
Issue number8
DOIs
Publication statusPublished - 2021 Apr 16

Bibliographical note

Funding Information:
We gratefully acknowledge the support from the National Research Foundation (NRF) of Korea grant funded by the Korean government (Nos. 2020R1C1C1014408 and 2020R1I1A1A01067730).

Publisher Copyright:
© 2021 American Chemical Society.

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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