Stereocontrolled Synthesis of 1, 2??Dialkyl??4??halopyrrolidines through PhSeX??Induced Cyclization of Secondary Homoallylamines

F Outurquin, X Pannecoucke, B Berthe…

Index: Outurquin, Francis; Pannecoucke, Xavier; Berthe, Benedicte; Paulmier, Claude European Journal of Organic Chemistry, 2002 , # 6 p. 1007 - 1014

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Citation Number: 22

Abstract

Abstract The selenium-induced cyclization of α-alkyl or α, α-dialkyl-homoallyl-benzylamines 1 by use of PhSeX (X= Cl, Br, I; 1.5 equiv.) provided a mixture of (phenylselanylmethyl) azetidines 2 and (phenylselanyl) pyrrolidines 3. 1 When an excess of PhSeX (X= Cl, Br) was used, 4-halopyrrolidines 4 (X= Cl) or 5 (X= Br) were formed and isolated in very good yields. Mono-or dialkyl 4-halopyrrolidines 4 and 5 could also be obtained stereospecifically by ...