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Synlett 2014; 25(16): 2275-2280
DOI: 10.1055/s-0034-1378564
DOI: 10.1055/s-0034-1378564
cluster
Novel Formal [3+3] Cycloaddition of Silyl Nitronates with Activated Cyclopropanes and Its Application in the Synthesis of Pyrroline-N-oxides
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.
Key words
formal [3+3] cycloaddition - silyl nitronates - donor–acceptor cyclopropanes - nitrogen heterocycles - ring contractionSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
- Supporting Information
-
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For reviews, see:
Selected examples:
Selected examples:
Selected examples:
Selected examples:
For cyclodimerization of cyclopropanes, see:
In our opinion the closest literature data are: