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

doi:10.1021/acs.orglett.1c00538

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 journal › Article › peer-review

2 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 language	English
Pages (from-to)	2904-2910
Number of pages	7
Journal	Organic Letters
Volume	23
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.1c00538
Publication status	Published - 2021 Apr 16

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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

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.",

author = "Lee, {Hyune Jea} and Yuya Yonekura and Nayoung Kim and Yoshida, {Jun Ichi} and Heejin Kim",

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: {\textcopyright} 2021 American Chemical Society.",

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doi = "10.1021/acs.orglett.1c00538",

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T1 - Regioselective Synthesis of α-Functional Stilbenes via Precise Control of Rapid cis- trans Isomerization in Flow

AU - Lee, Hyune Jea

AU - Yonekura, Yuya

AU - Kim, Nayoung

AU - Yoshida, Jun Ichi

AU - Kim, Heejin

N1 - 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.

PY - 2021/4/16

Y1 - 2021/4/16

N2 - 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.

AB - 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.

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DO - 10.1021/acs.orglett.1c00538

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SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

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

Abstract

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