Synthesis of substituted piperidines, decahydroquinolines and octahydroindolizines by radical rearrangement reactions of 2-alkylideneaziridines

Rearrangement of a variety of 3-(2-methyleneaziridin-1-yl)propyl radicals, generated using Bu 3SnH/AIBN by homolytic cleavage of phenylselenide substituted 2-methyleneaziridines, produces 3-methylenepiperidines in yields ranging from 58 to 68%. By combining this radical rearrangement with an additio...

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Bibliographic Details
Published in:Tetrahedron 2002-08, Vol.58 (35), p.7165-7175
Main Authors: Prévost, Natacha, Shipman, Michael
Format: Article
Language:English
Subjects:
aziridines
radicals and radical reactions
strained compounds
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Summary:Rearrangement of a variety of 3-(2-methyleneaziridin-1-yl)propyl radicals, generated using Bu 3SnH/AIBN by homolytic cleavage of phenylselenide substituted 2-methyleneaziridines, produces 3-methylenepiperidines in yields ranging from 58 to 68%. By combining this radical rearrangement with an additional 5- exo-trig cyclisation, this method provides an octahydroindolizine with moderate levels of diastereocontrol (d.r.=4:1). This rearrangement works with related 2-isopropylideneaziridines, but cannot be successfully extended to 4-(2-methyleneaziridin-1-yl)butyl radicals. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00730-5