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

  • Lee, Hyune-Jea; 
  • Yonekura, Yuya; 
  • Kim, Nayoung; 
  • Yoshida, Jun-ichi; 
  • Kim, Heejin
Citations

WEB OF SCIENCE

11
Citations

SCOPUS

14

초록

The rapid cis-trans isomerization of alpha-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 degrees 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.

키워드

ESTROGEN-RECEPTOR MODULATORS; POTENTIAL-ENERGY CURVES; FLASH CHEMISTRY; MULTIFUNCTIONAL MEDICINES; SERIAL MICROREACTIONS; ANTICANCER ACTIVITY; PLANT POLYPHENOLS; TAMOXIFEN; RESVERATROL; THERAPY
제목
Regioselective Synthesis of alpha-Functional Stilbenes via Precise Control of Rapid cis-trans Isomerization in Flow
저자
Lee, Hyune-Jea; Yonekura, Yuya; Kim, Nayoung; Yoshida, Jun-ichi; Kim, Heejin
DOI
10.1021/acs.orglett.1c00538
발행일
2021-04-16
유형
Article
저널명
Organic Letters
권
23
호
8
페이지
2904 ~ 2910