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Stereocontrolled Synthesis of 1,2‐Dialkyl‐4‐halopyrrolidines through PhSeX‐Induced Cyclization of Secondary Homoallylamines
Author(s) -
Outurquin Francis,
Pannecoucke Xavier,
Berthe Bénédicte,
Paulmier Claude
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200203)2002:6<1007::aid-ejoc1007>3.0.co;2-a
Subject(s) - chemistry , medicinal chemistry , decomposition , selenium , alkyl , stereochemistry , organic chemistry
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 SO 2 Cl 2 or Br 2 treatment of 4‐(phenylselanylmethyl)azetidines 2 , by way of the intermediate (halomethyl)azetidines 14 (X = Cl) or 15 (X = Br). When starting from 4‐(phenylselanyl)pyrrolidines 3 , monoalkylated 4‐halopyrrolidines 4 or 5 could be obtained stereospecifically after decomposition of the unstable dihaloselenuranes 16 and 17 . (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)