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Stereoselective synthesis of 2-aryl-4-en-1-ols, promising synthons for the preparation of oxygen heterocycles

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Abstract

Reactions of arylacetic acids with N-methoxymethanamine afford corresponding Weinreb amides which at alkenylation with methallyl and prenyl bromides in the presence of (Me3Si)2N–Na+ form unsaturated amides ArCHRCONMe(OMe) (R = CH2CMe=CH2, CH2C=CMe2). Amides readily react with BuLi and BnMgCl to give ketones ArCHRCOR' (R' = Bu, Bn). A stereoselective reduction of the latter with LiBH(s-Bu)3 leads to a quantitative formation of syn-isomers of 2-aryl-4-en-1-ols.

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Authors and Affiliations

  1. Timiryazev Moscow Agricultural Academy, Russian State Agricultural University, Timiryazevskaya ul. 49, Moscow, 127550, Russia

    V. I. Boev & S. L. Belopukhov

  2. Lipetsk State Pedagogical University, Lipetsk, Russia

    A. I. Moskalenko & G. N. Nikonova

Authors
  1. V. I. Boev
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  2. A. I. Moskalenko
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  3. S. L. Belopukhov
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  4. G. N. Nikonova
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Correspondence to V. I. Boev.

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Original Russian Text © V.I. Boev, A.I. Moskalenko, S.L. Belopukhov, G.N. Nikonova, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 2, pp. 182–190.

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Boev, V.I., Moskalenko, A.I., Belopukhov, S.L. et al. Stereoselective synthesis of 2-aryl-4-en-1-ols, promising synthons for the preparation of oxygen heterocycles. Russ J Org Chem 53, 169–177 (2017). https://doi.org/10.1134/S1070428017020051

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  • DOI: https://doi.org/10.1134/S1070428017020051

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