CYCLIZATION REACTIONS OF ALPHA-AMINO RADICALS DERIVED FROM N-(N',N'-DIALKYLAMINOALKENYL)BENZOTRIAZOLES AND SAMARIUM DIIODIDE

被引:32
作者
AURRECOECHEA, JM
FERNANDEZACEBES, A
机构
关键词
D O I
10.1016/0040-4039(93)85124-F
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-(N',N'-Dialkylaminoalkenyl)benzotriazoles, derived from secondary amines and unsaturated aldehydes, reacted with samarium diiodide (SmI2) to afford, through an alpha-amino radical intermediate, 5-exo and 6-exo cyclization products with good diastereoselectivity.
引用
收藏
页码:549 / 552
页数:4
相关论文
共 26 条
[1]   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
[2]   REGIO-SELECTIVITY AND STEREO-SELECTIVITY OF ALKENYL RADICAL RING-CLOSURE - A THEORETICAL-STUDY [J].
BECKWITH, ALJ ;
SCHIESSER, CH .
TETRAHEDRON, 1985, 41 (19) :3925-3941
[3]   ALPHA-ACYLAMINO RADICAL CYCLIZATIONS - APPLICATION TO THE SYNTHESIS OF A TETRACYCLIC SUBSTRUCTURE OF GELSEMINE [J].
CHOI, JK ;
HA, DC ;
HART, DJ ;
LEE, CS ;
RAMESH, S ;
WU, S .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (02) :279-290
[4]   THE SAMARIUM GRIGNARD REACTION - INSITU FORMATION AND REACTIONS OF PRIMARY AND SECONDARY ALKYLSAMARIUM(III) REAGENTS [J].
CURRAN, DP ;
TOTLEBEN, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :6050-6058
[5]   THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .1. [J].
CURRAN, DP .
SYNTHESIS-STUTTGART, 1988, (06) :417-439
[6]   THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .2. [J].
CURRAN, DP .
SYNTHESIS-STUTTGART, 1988, (07) :489-513
[7]   RADICAL REACTIONS AND RETROSYNTHETIC PLANNING [J].
CURRAN, DP .
SYNLETT, 1991, (02) :63-72
[8]   SYNTHESIS OF CYCLIC ALPHA-AMINO-ACIDS THROUGH RING-CLOSURE OF GLYCINE DERIVED FREE-RADICALS [J].
ESCH, PM ;
HIEMSTRA, H ;
SPECKAMP, WN .
TETRAHEDRON LETTERS, 1990, 31 (05) :759-762
[9]   RADICAL REACTIONS IN NATURAL PRODUCT SYNTHESIS [J].
JASPERSE, CP ;
CURRAN, DP ;
FEVIG, TL .
CHEMICAL REVIEWS, 1991, 91 (06) :1237-1286
[10]   ALPHA-ACYLAMINORADICAL ANNELATION IN THE DIASTEREOSELECTIVE SYNTHESIS OF 1-SUBSTITUTED AND 5-SUBSTITUTED TETRAHYDROPYRROLO[1,2-C]OXAZOLE AND 1-SUBSTITUTED PYRROLIZIDINE DERIVATIVES [J].
KANO, S ;
YUASA, Y ;
ASAMI, K ;
SHIBUYA, S .
CHEMISTRY LETTERS, 1986, (05) :735-736