Indium-mediated atom-transfer cyclizations and reductive cyclizations

被引:43
作者
Yanada, R [1 ]
Nishimori, N [1 ]
Matsumura, A [1 ]
Fujii, N [1 ]
Takemoto, Y [1 ]
机构
[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
关键词
D O I
10.1016/S0040-4039(02)00880-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel indium-mediated reactions have been studied. Treatment of iodoalkyne with In (0.5 equiv.) and I-2 (0.5 equiv.) in MeOH proanotes the atom-transfer 5-exo-cyclization. In contrast. the reaction with In (2 equiv.) and I-2 (I equiv.) gives rise to a reductive 5-exo-cyclized product. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4585 / 4588
页数:4
相关论文
共 51 条
[1]  
Baguley PA, 1998, ANGEW CHEM INT EDIT, V37, P3073, DOI 10.1002/(SICI)1521-3773(19981204)37:22<3072::AID-ANIE3072>3.0.CO
[2]  
2-9
[3]   Catalytic cycloisomerization of unsaturated organoiodides [J].
Bailey, WF ;
Carson, MW .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9960-9967
[4]   ZINC IRON COUPLE INDUCED CONJUGATE ADDITION OF ALKYL HALIDE DERIVED RADICALS TO ACTIVATED OLEFINS [J].
BLANCHARD, P ;
DASILVA, AD ;
ELKORTBI, MS ;
FOURREY, JL ;
ROBERTGERO, M .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (23) :6517-6519
[5]   Iodine transfer cyclization mediated by DIBAL-H/THF [J].
Chakraborty, A ;
Marek, I .
CHEMICAL COMMUNICATIONS, 1999, (23) :2375-2376
[6]   THE REPRODUCTIVE AND DEVELOPMENTAL TOXICITY OF INDIUM IN THE SWISS MOUSE [J].
CHAPIN, RE ;
HARRIS, MW ;
HUNTER, ES ;
DAVIS, BJ ;
COLLINS, BJ ;
LOCKHART, AC .
FUNDAMENTAL AND APPLIED TOXICOLOGY, 1995, 27 (01) :140-148
[7]   ORGANOSILANES AS RADICAL-BASED REDUCING AGENTS IN SYNTHESIS [J].
CHATGILIALOGLU, C .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (04) :188-194
[8]   ATOM-TRANSFER CYCLIZATION - A NOVEL ISOMERIZATION OF HEX-5-YNYL IODIDES TO (IODOMETHYLENE)CYCLOPENTANES [J].
CURRAN, DP ;
CHEN, MH ;
KIM, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (09) :2489-2490
[9]   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
[10]   ATOM TRANSFER CYCLIZATION REACTIONS OF HEX-5-YNYL IODIDES - SYNTHETIC AND MECHANISTIC STUDIES [J].
CURRAN, DP ;
CHEN, MH ;
KIM, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6265-6276