Synthesis of α-iodo-α,β-unsaturated ketones by the reaction of α-silyl-α,β-unsaturated ketones with ICl or ICl-AlCl3

被引:32
作者
Alimardanov, A [1 ]
Negishi, E [1 ]
机构
[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
关键词
alpha-iodo-alpha; beta-unsaturated ketones; alpha-silyl-alpha; ICl or ICl-AlCl3; iododesilylation;
D O I
10.1016/S0040-4039(99)00635-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of alpha-silyl-alpha,beta-unsaturated enones, readily preparable as regio- and stereodefined compounds in high yields, with either 2 equiv. of ICl or one equiv. each of ICl and AlCl3 provides the corresponding alpha-iodo-alpha,beta-unsaturated enones in high yields. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3839 / 3842
页数:4
相关论文
共 23 条
[1]   ALPHA-HALOENONES FROM SECONDARY ALKYNOLS [J].
ANGARA, GJ ;
MCNELIS, E .
TETRAHEDRON LETTERS, 1991, 32 (19) :2099-2100
[2]   NEW SYNTHETIC APPLICATIONS OF ORGANOTIN COMPOUNDS - SYNTHESIS OF STEREODEFINED 2-IODO-2-ALKENONES, 2-SUBSTITUTED (E)-2-ALKENONES AND 2-METHYL-2-CYCLOALKENONES [J].
BELLINA, F ;
CARPITA, A ;
CIUCCI, D ;
DESANTIS, M ;
ROSSI, R .
TETRAHEDRON, 1993, 49 (21) :4677-4698
[3]  
CHAN KS, 1994, TETRAHEDRON, V50, P2003
[4]  
DJUARDI E, 1997, SYNTHETIC COMMUN, V24, P2497
[5]   THE PREPARATION OF 2(1H)-PYRIDINONES AND 2,3-DIHYDRO-5(1H)-INDOLIZINONES VIA TRANSITION-METAL MEDIATED COCYCLIZATION OF ALKYNES AND ISOCYANATES - A NOVEL CONSTRUCTION OF THE ANTITUMOR AGENT CAMPTOTHECIN [J].
EARL, RA ;
VOLLHARDT, KPC .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (25) :4786-4800
[7]   TRIETHYLBORANE-INDUCED RADICAL-ADDITION OF ALKYL IODIDES TO ACETYLENES [J].
ICHINOSE, Y ;
MATSUNAGA, S ;
FUGAMI, K ;
OSHIMA, K ;
UTIMOTO, K .
TETRAHEDRON LETTERS, 1989, 30 (24) :3155-3158
[8]   DIRECT ALPHA-IODINATION OF CYCLOALKENONES [J].
JOHNSON, CR ;
ADAMS, JP ;
BRAUN, MP ;
SENANAYAKE, CBW ;
WOVKULICH, PM ;
USKOKOVIC, MR .
TETRAHEDRON LETTERS, 1992, 33 (07) :917-918
[9]   METAL-PROMOTED CYCLIZATION .11. REACTION OF ZIRCONOCENE DICHLORIDE WITH ALKYLLITHIUMS OR ALKYL GRIGNARD-REAGENTS AS A CONVENIENT METHOD FOR GENERATING A ZIRCONOCENE EQUIVALANT AND ITS USE IN ZIRCONIUM-PROMOTED CYCLIZATION OF ALKENES, ALKYNES, DIENES, ENYNES, AND DIYNES [J].
NEGISHI, E ;
CEDERBAUM, FE ;
TAKAHASHI, T .
TETRAHEDRON LETTERS, 1986, 27 (25) :2829-2832
[10]   METAL-PROMOTED CYCLIZATION .19. NOVEL BICYCLIZATION OF ENYNES AND DIYNES PROMOTED BY ZIRCONOCENE DERIVATIVES AND CONVERSION OF ZIRCONABICYCLES INTO BICYCLIC ENONES VIA CARBONYLATION [J].
NEGISHI, E ;
HOLMES, SJ ;
TOUR, JM ;
MILLER, JA ;
CEDERBAUM, FE ;
SWANSON, DR ;
TAKAHASHI, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3336-3346