Tetrahedron Letters

Stereospecific synthesis of 2, 3-disubstituted aziridines from β-alkylamino phenylselenides

S Boivin, F Outurquin, C Paulmier

Index: Boivin, Stephane; Outurquin, Francis; Paulmier, Claude Tetrahedron Letters, 2000 , vol. 41, # 5 p. 663 - 666

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Citation Number: 22

Abstract

Reduction of α-phenylselanyl imines derived from β-phenylselanyl α-oxoesters or PhSeCl assisted nucleophilic addition of primary amines to α, β-unsaturated esters have led to β- alkylamino phenylselenides 4, 5, 12 and 13 which were cyclised into aziridines 8, 9 and 14 after selenium activation. threo-Amino selenides led stereospecifically to cis-2, 3- disubstituted aziridines. Depending on the structure, non-functionalised amino selenides ...