Synlett 2014; 25(16): 2275-2280
DOI: 10.1055/s-0034-1378564
cluster
© Georg Thieme Verlag Stuttgart · New York

Novel Formal [3+3] Cycloaddition of Silyl Nitronates with Activated Cyclo­propanes and Its Application in the Synthesis of Pyrroline-N-oxides

Andrey A. Mikhaylov*
a  N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation   Fax: +7(95)1355328   Email: iof@ioc.ac.ru
,
Roman A. Novikov
a  N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation   Fax: +7(95)1355328   Email: iof@ioc.ac.ru
,
Yulia A. Khomutova
a  N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation   Fax: +7(95)1355328   Email: iof@ioc.ac.ru
,
Dmitry E. Arkhipov
b  A. N. Nesmeyanov Institute of Organoelement Compounds, Vavilova Str. 28, 119991 Moscow, Russian Federation
,
Alexander A. Korlyukov
b  A. N. Nesmeyanov Institute of Organoelement Compounds, Vavilova Str. 28, 119991 Moscow, Russian Federation
,
Andrey A. Tabolin
a  N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation   Fax: +7(95)1355328   Email: iof@ioc.ac.ru
,
Yury V. Tomilov
a  N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation   Fax: +7(95)1355328   Email: iof@ioc.ac.ru
,
Sema L. Ioffe*
a  N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation   Fax: +7(95)1355328   Email: iof@ioc.ac.ru
› Author Affiliations
Further Information

Publication History

Received: 12 May 2014

Accepted after revision: 14 July 2014

Publication Date:
11 August 2014 (online)


Abstract

1,1-Cyclopropane diesters with donor substituents undergo formal [3+3] cycloaddition with various silyl nitronates under Yb(OTf)3 catalysis in the presence of a proton scavenger to give target N-silyloxy tetrahydro-1,2-oxazines in 56–98% yield. The reasons determining the reaction diastereoselectivity are discussed. The resulting tetrahydro-1,2-oxazines are transformed into pyrroline-N-oxides via a novel TfOH-promoted silanol elimination reaction.

Supporting Information

 
  • References and Notes


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