Synthesis of 2,3-disubstituted pyrrolidines by intramolecular addition of α-aminoalkyl radicals to electron deficient C=C bonds

被引:41
作者
Aurrecoechea, JM [1 ]
Fernández, A [1 ]
Gorgojo, JM [1 ]
Saornil, C [1 ]
机构
[1] Univ Basque Country, Fac Ciencias, Dept Quim Organ, E-48080 Bilbao, Spain
关键词
cyclization; pyrrolidines; radicals; samarium;
D O I
10.1016/S0040-4020(99)00359-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2,3-Disubstituted pyrrolidines are prepared by SmI2-pranoted cyclization of alpha-amino radicals generated from N-(alpha-benzotriazolylalkyl)alkenylamines containing a C=C bond activated by an electron withdrawing substituent. The diastereoselectivity of cyclization is moderate and depends on the nature of the substituent at the pyrrolidine 2-position. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7345 / 7362
页数:18
相关论文
共 91 条
[1]   Synthesis of heterocycles by radical cyclisation [J].
Aldabbagh, F ;
Bowman, WR .
CONTEMPORARY ORGANIC SYNTHESIS, 1997, 4 (04) :261-280
[2]   Diastereoselective 5-exo-trig radical cyclisation on N-acryloyl-tetrahydro-1,3-oxazines. A novel approach to enantiopure 3-substituted pyrrolidines [J].
Andres, C ;
DuqueSoladana, JP ;
Iglesias, JM ;
Pedrosa, R .
TETRAHEDRON LETTERS, 1996, 37 (50) :9085-9086
[3]   SYNTHESIS OF VICINAL DIAMINES BY SMI2-PROMOTED REDUCTION OF N-(N',N'-DIALKYLAMINOALKYL)BENZOTRIAZOLES [J].
AURRECOECHEA, JM ;
FERNANDEZACEBES, A .
TETRAHEDRON LETTERS, 1992, 33 (33) :4763-4766
[4]  
Aurrecoechea JM, 1996, SYNLETT, P39
[5]   Diastereoselective synthesis of cycloalkylamines by samarium diiodide-promoted cyclizations of alpha-amino radicals derived from alpha-benzotriazolylalkenylamines [J].
Aurrecoechea, JM ;
Lopez, B ;
Fernandez, A ;
Arrieta, A ;
Cossio, FP .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04) :1125-1135
[6]   Enantioselective total synthesis of (-)-alpha-kainic acid through free radical cyclization of an alkenyl monothioformimide [J].
Bachi, MD ;
Melman, A .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1896-1898
[7]  
Baker SR, 1998, TETRAHEDRON LETT, V39, P7197
[8]  
BALDWIN JE, 1994, TETRAHEDRON, V50, P9425, DOI 10.1016/S0040-4020(01)85517-4
[9]   THE SYNTHESIS OF SUBSTITUTED PYRROLIDINES BY A SAMARIUM(II) IODIDE-MEDIATED RING-CLOSURE .1. [J].
BALDWIN, JE ;
MACKENZIETURNER, SC ;
MOLONEY, MG .
TETRAHEDRON, 1994, 50 (31) :9411-9424
[10]   CENTENARY LECTURE - THE PURSUIT OF SELECTIVITY IN RADICAL REACTIONS [J].
BECKWITH, ALJ .
CHEMICAL SOCIETY REVIEWS, 1993, 22 (03) :143-151