Rhodium-catalysed substitutive arylation of cis-allylic diols with arylboroxines

被引:58
作者
Miura, Tomoya [1 ]
Takahashi, Yusuke [1 ]
Murakami, Masahiro [1 ]
机构
[1] Kyoto Univ, Dept Synth Chem & Biol Chem, Kyoto 6158510, Japan
关键词
D O I
10.1039/b612710j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Substitutive arylation of cis-allylic diols occurs upon treatment with arylboroxines in the presence of a rhodium(I) catalyst; the reaction proceeds through the addition of an intermediate arylrhodium(I) species across the carbon-carbon double bond and subsequent beta-oxygen elimination.
引用
收藏
页码:595 / 597
页数:3
相关论文
共 25 条
[1]   BETA-VINYL-GAMMA-BUTYROLACTONES VIA THE PALLADIUM-CATALYZED REACTION OF VINYL TRIFLATES WITH Z-2-BUTEN-1,4-DIOL [J].
ARCADI, A ;
BERNOCCHI, E ;
CACCHI, S ;
MARINELLI, F .
TETRAHEDRON, 1991, 47 (08) :1525-1540
[2]   PALLADIUM-CATALYZED VINYL SUBSTITUTION-REACTIONS .1. NEW SYNTHESIS OF 2-PHENYL AND 3-PHENYL SUBSTITUTED ALLYLIC ALCOHOLS, ALDEHYDES, AND KETONES FROM ALLYLIC ALCOHOLS [J].
CHALK, AJ ;
MAGENNIS, SA .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (02) :273-278
[3]   Asymmetric nitroallylation of arylboronic acids with nitroallyl acetates catalyzed by chiral rhodium complexes and its application in a concise total synthesis of optically pure (+)-γ-lycorane [J].
Dong, L ;
Xu, YJ ;
Cun, LF ;
Cui, X ;
Mi, AQ ;
Jiang, YZ ;
Gong, LZ .
ORGANIC LETTERS, 2005, 7 (19) :4285-4288
[4]   Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].
Fagnou, K ;
Lautens, M .
CHEMICAL REVIEWS, 2003, 103 (01) :169-196
[5]   Catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of organoboronic acids.: Arylrhodium, oxa-π-allylrhodium, and hydroxorhodium intermediates [J].
Hayashi, T ;
Takahashi, M ;
Takaya, Y ;
Ogasawara, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (18) :5052-5058
[6]   A CONVENIENT METHOD FOR DIHYDROXYLATION OF OLEFINS BY THE COMBINED USE OF OSMIUM-TETROXIDE AND DIHYDROXYPHENYLBORANE [J].
IWASAWA, N ;
KATO, T ;
NARASAKA, K .
CHEMISTRY LETTERS, 1988, (10) :1721-1724
[7]   Rhodium-catalyzed cross-coupling of allyl alcohols with aryl- and vinylboronic acids in ionic liquids [J].
Kabalka, GW ;
Dong, G ;
Venkataiah, B .
ORGANIC LETTERS, 2003, 5 (06) :893-895
[8]   Rhodium-catalyzed asymmetric ring opening of oxabicyclic alkenes with organoboronic acids [J].
Lautens, M ;
Dockendorff, C ;
Fagnou, K ;
Malicki, A .
ORGANIC LETTERS, 2002, 4 (08) :1311-1314
[9]   Rhodium-catalyzed coupling reactions of arylboronic acids to olefins in aqueous media [J].
Lautens, M ;
Roy, A ;
Fukuoka, K ;
Fagnou, K ;
Martín-Matute, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (22) :5358-5359
[10]  
MANDAI T, 1990, SYNLETT, P85