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

Authors
Lee, Hyune-JeaYonekura, YuyaKim, NayoungYoshida, Jun-ichiKim, Heejin
Issue Date
16-4월-2021
Publisher
AMER CHEMICAL SOC
Citation
ORGANIC LETTERS, v.23, no.8, pp.2904 - 2910
Indexed
SCIE
SCOPUS
Journal Title
ORGANIC LETTERS
Volume
23
Number
8
Start Page
2904
End Page
2910
URI
https://scholar.korea.ac.kr/handle/2021.sw.korea/137453
DOI
10.1021/acs.orglett.1c00538
ISSN
1523-7060
Abstract
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.
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