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Synthesis 2020; 52(04): 602-608
DOI: 10.1055/s-0039-1690243
paper
© Georg Thieme Verlag Stuttgart · New York

BF3·OEt2-Catalyzed Synthesis of anti-β-(N-Arylamino)-α-hydroxynitriles by Regio- and Diastereospecific Ring Opening of 3-Aryloxirane-2-carbonitriles with Anilines

Chuangchuang Xu
,
Yang Lu
,
Kaini Xu
,
Jiaxi Xu∗
State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, People’s Republic of China   eMail: jxxu@mail.buct.edu.cn
› InstitutsangabenThis work was supported by the National Natural Science Foundation of China (Nos. 21572017 and 21772010) and the Fundamental Research Funds for the Central Universities (XK1802-6).
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Publikationsverlauf

Received: 13. August 2019

Accepted after revision: 15. Oktober 2019

Publikationsdatum:
05. November 2019 (online)

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Abstract

A safe and convenient synthetic method to anti-β-(N-arylamino)-α-hydroxynitriles from 3-aryloxirane-2-carbonitriles and anilines was developed under the catalysis of BF3·OEt2 in ethanol. In this method, BF3·OEt2 first reacts with ethanol to produce the true catalyst of super­ acid H[B(OEt)F3], followed by an acid-catalyzed regio- and diastereospecific ring opening of oxirane-2-carbonitriles with anilines, generating anti-β-(N-arylamino)-α-hydroxynitriles. The method features the advantages of non-metal catalysis, short reaction times, and easy operation, and uses an environmentally friendly solvent.

Key words

amino-hydroxynitrile - boron trifluoride - ring opening - regiospecificity­ - diastereospecificity - oxiranecarbonitrile - aniline

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690243.
  • Supporting Information
 

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