Tandem Gold-Catalyzed HydrosilyloxylationAldol and Mannich Reaction with Alkynylaryloxysilanols in 6-exo Mode

被引：13

作者：

Lee, Euichul ^{[1
]}

Ryu, Taekyu ^{[1
]}

Park, Youngchul ^{[1
]}

Park, Sangjune ^{[1
]}

Lee, Phil Ho ^{[1
]}

机构：

[1] Kangwon Natl Univ, Dept Chem, Chunchon 200701, South Korea

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 08期

基金：

新加坡国家研究基金会;

关键词：

aldol reaction; 6-exo mode; gold; hydrosilyloxylation; Mannich reaction; CONTAINING AZOMETHINE YLIDES; TERMINAL ALKYNES; ALPHA; BETA-UNSATURATED KETONES; INTRAMOLECULAR CYCLIZATION; REGIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; ADDITION-REACTION; ASYMMETRIC ALDOL; ALLYLIC ALCOHOLS; ISOMERIZATION;

D O I：

10.1002/adsc.201300244

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The tandem gold-catalyzed hydrosilyloxylationaldol and hydrosilyloxylationMannich reactions were developed through the formation of an enol silyl ether catalytically generated in situ from alkynylaryloxysilanols in the 6-exo mode in one reaction vessel.

引用

页码：1585 / 1596

页数：12

共 74 条

[1] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].

Alonso, F ;

Beletskaya, IP ;

Yus, M .

CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159

[2] Catalytic and selective conversion of (Z)-2-en-4-ynoic acids to either 2H-pyran-2-ones in the presence of ZnBr2 or (Z)-5-alkylidenefuran-2(5H)-ones in the presence of Ag2CO3 [J].

Anastasia, L ;

Xu, C ;

Negishi, E .

TETRAHEDRON LETTERS, 2002, 43 (32) :5673-5676

[3]

[Anonymous], 2010, ANGEW CHEM INT ED, V49, P6806

[4]

[Anonymous], 1979, ANGEW CHEM INT ED, V18, P837

[5]

[Anonymous], 1998, ANGEW CHEM INT ED, V37, P1044

[6]

Arend M., 1998, ANGEW CHEM, V110, P1096, DOI DOI 10.1002/(SICI)1521-3757(19980420)110:8

[7] Synthesis of 2,3-dihydroisoxazoles from propargylic N-hydroxylamines via Zn(II)-catalyzed ring-closure reaction [J].

Aschwanden, P ;

Frantz, DE ;

Carreira, EM .

ORGANIC LETTERS, 2000, 2 (15) :2331-2333

[8] REGIO-SELECTIVE, DIASTEREO-SELECTIVE, AND ENANTIO-SELECTIVE CONDENSATION OF CHIRAL VINYLIC BORATES WITH ALDEHYDES [J].

BASILE, T ;

BIONDI, S ;

BOLDRINI, GP ;

TAGLIAVINI, E ;

TROMBINI, C ;

UMANIRONCHI, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (05) :1025-1029

[9] Synthesis of 2-arylbenzo[b]furans via copper(I)-catalyzed coupling of o-iodophenols and aryl acetylenes [J].

Bates, CG ;

Saejueng, P ;

Murphy, JM ;

Venkataraman, D .

ORGANIC LETTERS, 2002, 4 (26) :4727-4729

[10] Regioselective synthesis of natural and unnatural (Z)-3-(1-alkylidene)phthalides and 3-substituted isocoumarins starting from methyl 2-hydroxybenzoates [J].

Bellina, F ;

Ciucci, D ;

Vergamini, P ;

Rossi, R .

TETRAHEDRON, 2000, 56 (16) :2533-2545

← 1 2 3 4 5 6 7 8 →