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Diastereoselective ...
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
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Ray, C. A. (författare)
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Risberg, E. (författare)
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- Somfai, Peter (författare)
- KTH,Kemi
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(creator_code:org_t)
- 2002
- 2002
- Engelska.
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Ingår i: Tetrahedron. - 0040-4020 .- 1464-5416. ; 58:30, s. 5983-5987
- Relaterad länk:
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https://urn.kb.se/re...
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visa fler...
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https://doi.org/10.1...
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Abstract
Ämnesord
Stäng
- 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.
Nyckelord
- azirine
- azifidine
- hetero Diels-Alder reaction
- diels-alder reactions
- dienophiles
- 2h-azirines
Publikations- och innehållstyp
- ref (ämneskategori)
- art (ämneskategori)
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