Synthesis 2014; 46(06): 771-780
DOI: 10.1055/s-0033-1340479
paper
© Georg Thieme Verlag Stuttgart · New York

A Highly Efficient and Stereoselective Cycloaddition of Nitrones to N-Vinylpyrroles

Authors

  • Alexander P. Molchanov*

    a   Department of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russian Federation   Fax: +7(812)4286939   eMail: s.lab@pobox.spbu.ru
  • Ruslan S. Savinkov

    a   Department of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russian Federation   Fax: +7(812)4286939   eMail: s.lab@pobox.spbu.ru
  • Alexander V. Stepakov

    a   Department of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russian Federation   Fax: +7(812)4286939   eMail: s.lab@pobox.spbu.ru
  • Galina L. Starova

    a   Department of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russian Federation   Fax: +7(812)4286939   eMail: s.lab@pobox.spbu.ru
  • Rafael R. Kostikov

    a   Department of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russian Federation   Fax: +7(812)4286939   eMail: s.lab@pobox.spbu.ru
  • Victoriya S. Barnakova

    b   A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation
  • Andrey V. Ivanov

    b   A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation
Weitere Informationen

Publikationsverlauf

Received: 02. Oktober 2013

Accepted after revision: 29. November 2013

Publikationsdatum:
07. Februar 2014 (online)


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Abstract

1,3-Dipolar cycloadditions of a number of C-aryl, C-carbamoyl-, and C,C-bis(methoxycarbonyl)nitrones and substituted N-vinylpyrroles proceed with high efficiency and regioselectivity with the formation of only one isomeric substituted 5-(1H-pyrrol-1-yl)isoxazolidine cycloadduct.