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

N Prévost, M Shipman

Index: Prevost, Natacha; Shipman, Michael Tetrahedron, 2002 , vol. 58, # 35 p. 7165 - 7175

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Citation Number: 32

Abstract

Rearrangement of a variety of 3-(2-methyleneaziridin-1-yl) propyl radicals, generated using Bu3SnH/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 (dr= 4: 1). This ...