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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

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
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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.

Key words

pyrroles - nitrones - isoxazolidines - cycloaddition - stereo­selectivity
 

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