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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
- Artikel/kapitelEngelska2002
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Nummerbeteckningar
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LIBRIS-ID:oai:DiVA.org:kth-21752
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https://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-21752URI
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https://doi.org/10.1016/S0040-4020(02)00611-7DOI
Kompletterande språkuppgifter
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Språk:engelska
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Sammanfattning på:engelska
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Klassifikation
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Ämneskategori:ref swepub-contenttype
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Ämneskategori:art swepub-publicationtype
Anmärkningar
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QC 20100525
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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.
Ämnesord och genrebeteckningar
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azirine
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azifidine
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hetero Diels-Alder reaction
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diels-alder reactions
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dienophiles
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2h-azirines
Biuppslag (personer, institutioner, konferenser, titlar ...)
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Risberg, E.
(författare)
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Somfai, PeterKTH,Kemi(Swepub:kth)u1ddelvn
(författare)
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KTHKemi
(creator_code:org_t)
Sammanhörande titlar
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Ingår i:Tetrahedron58:30, s. 5983-59870040-40201464-5416
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