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 MODULATORSPOTENTIAL-ENERGY CURVESFLASH CHEMISTRYMULTIFUNCTIONAL MEDICINESSERIAL MICROREACTIONSANTICANCER ACTIVITYPLANT POLYPHENOLSTAMOXIFENRESVERATROLTHERAPY
제목
Regioselective Synthesis of alpha-Functional Stilbenes via Precise Control of Rapid cis-trans Isomerization in Flow
저자
Lee, Hyune-JeaYonekura, YuyaKim, NayoungYoshida, Jun-ichiKim, Heejin
DOI
10.1021/acs.orglett.1c00538
발행일
2021-04-16
유형
Article
저널명
Organic Letters
23
8
페이지
2904 ~ 2910