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
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
收藏
页码:1585 / 1596
页数:12
相关论文
共 74 条
[11]   ASYMMETRIC ALDOL REACTIONS USING (4R-TRANS)-2-(1-METHYL-ETHENYL)-1,3,2-DIOXABOROLANE-4,5-DICARBOXYLIC ACID, BIS-ETHYL ESTER, A CHIRAL PRECURSOR OF THE ACETONE ENOLATE [J].
BOLDRINI, GP ;
LODI, L ;
TAGLIAVINI, E ;
TROMBINI, C ;
UMANIRONCHI, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 336 (1-2) :23-28
[12]   Silylene transfer to carbonyl compounds and subsequent Ireland-Claisen rearrangements to control formation of quaternary carbon stereocenters [J].
Calad, SA ;
Woerpel, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (07) :2046-2047
[13]   Gold(I)-Catalyzed Cyclization of Alkynyl Hydrogen Phosphates [J].
Chary, Bathoju Chandra ;
Low, Wee Suan ;
Kim, Sunggak ;
Kim, Hyunseok ;
Lee, Phil Ho .
CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (08) :1970-1973
[14]  
Cowden C.J., 1997, Org. React. (New York), V51, P1
[15]   From allylic alcohols to aldols via a novel, tandem isomerization-condensation catalyzed by Fe(CO)5 [J].
Crévisy, C ;
Wietrich, M ;
Le Boulaire, V ;
Uma, R ;
Grée, R .
TETRAHEDRON LETTERS, 2001, 42 (03) :395-398
[16]   Stereoselective synthesis of vancosamine and saccharosamine glycals via tungsten-catalyzed alkynol cycloisomerization [J].
Cutchins, WW ;
McDonald, FE .
ORGANIC LETTERS, 2002, 4 (05) :749-752
[17]  
Denmark S.E., 1999, COMPREHENSIVE ASYMME, P923
[18]  
Edwards G. L., 1991, CHEM COMMUN, P1399
[19]  
Evans D.A., 1982, TOP STEREOCHEM, V13, P1, DOI DOI 10.1002/9780470147221.CHL
[20]  
Franklin A.S., 1994, Contemp. Org. Synth, V1, P317