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

Alexander P. Molchanov; Ruslan S. Savinkov; Alexander V. Stepakov; Galina L. Starova; Rafael R. Kostikov; Victoriya S. Barnakova; Andrey V. Ivanov

doi:10.1055/s-0033-1340479

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(06): 771-780
DOI: 10.1055/s-0033-1340479

paper

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

Alexander P. Molchanov*

^aDepartment 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

^aDepartment 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

^aDepartment 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

^aDepartment 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

^aDepartment 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

^bA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation

,

Andrey V. Ivanov

^bA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation

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Abstract

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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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Referenzen

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