New Modes for the Osmium-Catalyzed Oxidative Cyclization

New Modes for the Osmium-Catalyzed Oxidative Cyclization

The osmium-catalyzed oxidative cyclization of amino alcohol initiators formally derived from 1,4-dienes is an effective method for the construction of pyrrolidines, utilizing a novel reoxidant (4-nitropyridine N-oxide = NPNO). The cyclization of enantiopure syn- and anti-amino alcohols gives rise to...

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Veröffentlicht in:Organic letters 2010-03, Vol.12 (5), p.1060-1063
Hauptverfasser: Donohoe, Timothy J, Lindsay-Scott, Peter J, Parker, Jeremy S, Callens, Cedric K. A
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Cyclization
Models, Molecular
Molecular Conformation
Osmium - chemistry
Oxidation-Reduction
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Zusammenfassung:The osmium-catalyzed oxidative cyclization of amino alcohol initiators formally derived from 1,4-dienes is an effective method for the construction of pyrrolidines, utilizing a novel reoxidant (4-nitropyridine N-oxide = NPNO). The cyclization of enantiopure syn- and anti-amino alcohols gives rise to enantiopure cis- and trans-2,5-disubstituted pyrrolidines, respectively. Moreover, the cyclization of bis-homoallylic amines bearing an exocyclic chelating group is shown to be a complementary method for trans-pyrrolidine formation.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol100046a