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Diastereoselective Lewis acid-catalysed 4+2 cycloadditions of 3-alkyl-, 3-aryl- and 3-carboxyl-2H-azirines: a route to aziridine containing azabicyclo 4.1.0 heptanes and azatricyclo 2.2.1.0 nonanes
KTH, Superseded Departments, Chemistry.
2002 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 58, no 30, 5983-5987 p.Article in journal (Refereed) Published
Abstract [en]

3-Substituted-2H-azirines have been employed as 2pi components in Lewis acid-catalysed hetero Diels-Alder reactions with a variety of diene systems. A series of Lewis acids were screened for catalytic behaviour in the reaction between Danishefsky's diene and 3-phenyl-2H-azirine to give the cycloaddition adduct, and in most cases elevated temperature were required to effect cycloaddition. A noteworthy exception was a BF3.Et2O-catalysed cycloaddition which proceeded in less than I h between -70degreesC and -60degreesC. The cycloadditions were found to proceed with endo selectivity providing a single diastereoisomeric product. Benzyl 2H-azirine-3-carboxylates were found to be activated by Lewis acids and participate in endo selective cycloadditions at -20degreesC.

Place, publisher, year, edition, pages
2002. Vol. 58, no 30, 5983-5987 p.
Keyword [en]
azirine, azifidine, hetero Diels-Alder reaction, diels-alder reactions, dienophiles, 2h-azirines
Identifiers
URN: urn:nbn:se:kth:diva-21752ISI: 000177028600003OAI: oai:DiVA.org:kth-21752DiVA: diva2:340450
Note
QC 20100525Available from: 2010-08-10 Created: 2010-08-10 Last updated: 2017-12-12Bibliographically approved

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