Strong counteranion effects on the catalytic activity of cationic silicon Lewis acids in Mukaiyama aldol and Diels-Alder reactions

被引：94

作者：

Hara, K ^{[1
]}

Akiyama, R ^{[1
]}

Sawamura, M ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Sci, Div Chem, Sapporo, Hokkaido 0600810, Japan

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 25期

关键词：

D O I：

10.1021/ol052206g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A toluene-coordinated silyl borate, [Et3Si(toluene)]B(C6F5)(4), demonstrated catalytic activities significantly higher than those of Me3SiOTf and Me3SiNTf2 in Mukaiyama aldol and Diels-Alder reactions.

引用

页码：5621 / 5623

页数：3

共 22 条

[1] Carbon-carbon bond forming reactions mediated by silicon Lewis acids [J].

Dilman, AD ;

Ioffe, SL .

CHEMICAL REVIEWS, 2003, 103 (03) :733-772

[2]

HATANAKA Y, 2001, 81 SPRING M CHEM SOC

[3] HOMOGENEOUS CATALYSIS - [TICP2(CF3SO3)2] AND [ZRCP2(CF3SO3)2THF], FAST AND EFFICIENT CATALYSTS FOR THE MUKAIYAMA CROSS-ALDOL REACTION [J].

HOLLIS, TK ;

ROBINSON, NP ;

BOSNICH, B .

TETRAHEDRON LETTERS, 1992, 33 (43) :6423-6426

[4]

Ishihara K, 2001, SYNLETT, P1851

[5]

Ishihara K, 2001, SYNLETT, P394

[6]

Ishii A, 1997, SYNLETT, P1145

[7] Synthesis and application of the first chiral and highly Lewis acidic silyl cationic catalyst [J].

Johannsen, M ;

Jorgensen, KA ;

Helmchen, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (30) :7637-7638

[8] CHEMISTRY OF ORGANOSILICON COMPOUNDS .292. AN NMR-STUDY OF THE FORMATION OF SILYLOXONIUM IONS BY USING TETRAKIS[3,5-BIS(TRIFLUOROMETHYL)PHENYL]BORATE AS COUNTERANION [J].

KIRA, M ;

HINO, T ;

SAKURAI, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (17) :6697-6700

[9] TETRAKIS(PENTAFLUOROPHENYL)BORATE - A NEW ANION FOR SILYLIUM CATIONS IN THE CONDENSED PHASE [J].

LAMBERT, JB ;

ZHANG, SH .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (04) :383-384

[10] MODERN APPROACHES TO SILYLIUM CATIONS IN CONDENSED-PHASE [J].

LAMBERT, JB ;

KANIA, L ;

ZHANG, SZ .

CHEMICAL REVIEWS, 1995, 95 (05) :1191-1201

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