(E)-,(Z)-parallel preparative methods for stereodefined β,β-diaryl- and α,β-diaryl-α,β-unsaturated esters: application to the stereocomplementary concise synthesis of zimelidine

Chemistry : a European Journal
Yuichiro AshidaYoo Tanabe

Abstract

Parallel and practical methods for the preparation of both (E)- and (Z)-β-aryl(1)-β-aryl(2)-α,β-unsaturated esters 1 and (E)- and (Z)-α-aryl(1)-β-aryl(2)-α,β-unsaturated esters 2 are described. These methods involve accessible, robust, stereocomplementary N-methylimidazole (NMI)-mediated enol tosylations (14 examples, 70-99% yield), as well as stereoretentive Suzuki-Miyaura cross-couplings (36 examples, 64-99% yield). The highlighted feature of the present protocol is the use of parallel and stereocomplementary approaches to obtain highly (E)- and (Z)-pure products 1 and 2 by utilizing sequential enol tosylations and cross-coupling reactions. An expeditious and parallel synthesis of (E)- and (Z)-zimelidine (3), which is a highly representative selective serotonin reuptake inhibitor (SSRI), was performed by utilizing the present methods.

References

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May 22, 2004·The Journal of Organic Chemistry·Mitsuru ShindoKozo Shishido
Mar 12, 2005·Organic Letters·Artis KlaparsRalph P Volante
Mar 31, 2005·Journal of the American Chemical Society·Timothy E BarderStephen L Buchwald
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May 29, 2008·Chemistry : a European Journal·Anders T Lindhardt, Troels Skrydstrup
Jun 10, 2008·Chemical Communications : Chem Comm·Yoshihiko YamamotoYu Harada

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Citations

Aug 19, 2015·The Journal of Organic Chemistry·Masaharu SugiuraMakoto Nakajima
Apr 27, 2017·Organic & Biomolecular Chemistry·Yuyang ZhaoZhiming Wang
Jan 3, 2020·Chemical Communications : Chem Comm·Yi-Ming WeiXin-Fang Duan
Sep 16, 2020·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Yuichiro Ashida, Yoo Tanabe
Jan 20, 2021·Journal of the American Chemical Society·Yaroslav D BoykoDavid Sarlah
Apr 29, 2021·Chemical Communications : Chem Comm·Floris ButtardPier Alexandre Champagne

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