Triethylborane-mediated atom-transfer cyclisation of 2-iodo-N-(prop-2-enyl)acetamides and related compounds

被引：30
作者：
Ikeda, M
Teranishi, H
Nozaki, K
Ishibashi, H [1 ]
机构：
[1] Kyoto Pharmaceut Univ, Kyoto 6078414, Japan
[2] Kanazawa Univ, Fac Pharmaceut Sci, Kanazawa, Ishikawa 9200934, Japan
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 10期
关键词：
D O I：
10.1039/a800402a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The 2-iodo-N-(prop-2-enyl)acetamides 1, upon treatment with triethylborane (0.2-0.6 mol equiv.) in boiling benzene, undergo iodine atom-transfer cyclisation to give the 4-(iodomethyl)pyrrolidin-2-ones 2 in high yields. The method has been applied to the synthesis of gamma-lactones.
引用
收藏
页码：1691 / 1697
页数：7
相关论文
共 32 条
[21]   INDIRECT ELECTROREDUCTIVE CYCLIZATION OF N-ALLYLIC AND N-PROPARGYLBROMO AMIDES AND O-BROMOACRYLOYLANILIDES USING NICKEL(II) COMPLEXES AS ELECTRON-TRANSFER CATALYSTS [J].
OZAKI, S ;
MATSUSHITA, H ;
OHMORI, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (19) :2339-2344
[22]  
OZAKI S, 1995, CHEM PHARM BULL, V43, P863
[23]   SODIUM-BOROHYDRIDE REDUCTIONS UNDER PHASE-TRANSFER CONDITIONS - CONVERSION OF HALIDES AND SULFONATE ESTERS TO ALKANES [J].
ROLLA, F .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3909-3911
[24]   SYNTHESIS OF PYRROLIDIN-2-ONES BY 5-ENDO-TRIGOPLAL RADICAL CYCLIZATION OF N-VINYL-2,2-BIS(PHENYLSULFANYL)ACETAMIDES [J].
SATO, T ;
CHONO, N ;
ISHIBASHI, H ;
IKEDA, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (09) :1115-1120
[25]  
SATO T, 1992, CHEM PHARM BULL, V40, P2308
[26]   REGIOCHEMISTRY OF RADICAL CYCLIZATIONS (6-EXO/7-ENDO AND 7-EXO/8-ENDO) OF N-(O-ALKENYLPHENYL)-2,2-DICHLOROACETAMIDES [J].
SATO, T ;
ISHIDA, S ;
ISHIBASHI, H ;
IKEDA, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (02) :353-359
[27]   SYNTHESIS OF 5-MEMBERED LACTAMS BY ALPHA-CARBAMOYL RADICAL CYCLIZATIONS [J].
SATO, T ;
WADA, Y ;
NISHIMOTO, M ;
ISHIBASHI, H ;
IKEDA, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (05) :879-886
[28]   FORMATION OF 5-MEMBERED LACTAMS BY 5-ENDO-TRIGONAL RADICAL CYCLIZATIONS OF 2-CHLORO-N-(CYCLOALK-1-ENYL)ACETAMIDES - NEW SYNTHESIS OF ERYTHRINANE SKELETON [J].
SATO, T ;
NAKAMURA, N ;
IKEDA, K ;
OKADA, M ;
ISHIBASHI, H ;
IKEDA, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (18) :2399-2407
[29]   SYNTHESIS OF PYRROLIZIDINES VIA COPPER(I) CATALYZED RADICAL ATOM TRANSFER CYCLIZATION [J].
SEIJAS, JA ;
VAZQUEZTATO, MP ;
CASTEDO, L ;
ESTEVEZ, RJ ;
ONEGA, MG ;
RUIZ, M .
TETRAHEDRON, 1992, 48 (09) :1637-1642
[30]   RADICAL CYCLIZATION OF ALLYLIC HALOACETAMIDES - A ROUTE TO CIS-FUSED 2-PYRROLIDONES AND PIPERIDONES [J].
STORK, G ;
MAH, R .
HETEROCYCLES, 1989, 28 (02) :723-727
1234