Rhenium-catalyzed reaction of carbonyl compounds with ketene silyl acetals

被引:17
作者
Nishiyama, Yutaka [1 ]
Kaiba, Kenta [1 ]
Umeda, Rui [1 ]
机构
[1] Kansai Univ, Fac Chem Mat & Bioengn, Dept Chem & Mat Engn, Osaka 5648680, Japan
关键词
ENANTIOSELECTIVE MUKAIYAMA ALDOL; LEWIS-ACID; MICHAEL REACTIONS; ENOL ETHERS; PARALLEL RECOGNITION; ALLYLATION; COMPLEXES; ALDEHYDES; DIFFERENTIATION; ALKYLATION;
D O I
10.1016/j.tetlet.2009.11.109
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
It was found that rhenium complex is an effective catalyst for the reaction of carbonyl compounds with ketene silyl acetals. A wide range of beta-silyloxy esters is obtained by the treatment of carbonyl compounds with ketene silyl acetals in the presence of a catalytic amount of ReBr(CO)(5) in moderate to good yields. (c) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:793 / 795
页数:3
相关论文
共 33 条
[1]   Switchable reactivity of acylated α,β-dehydroamino ester in the Friedel-Crafts alkylation of indoles by changing the Lewis acid [J].
Angelini, Elena ;
Balsamini, Cesarino ;
Bartoccini, Francesca ;
Lucarini, Simone ;
Piersanti, Giovanni .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14) :5654-5657
[2]   Enantioselective Mukaiyama aldol and Sakurai allylation reactions catalysed by silver(I) complexes with chiral atropisomeric chelating ligands [J].
Cesarotti, E ;
Araneo, S ;
Rimoldi, I ;
Tassi, S .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2003, 204 (204-205) :221-226
[3]   Unusual preference for ketone and reversal of chemoselectivity in Lewis acid-catalyzed aldol reaction of ketene silyl acetal [J].
Chen, JX ;
Sakamoto, K ;
Orita, A ;
Otera, J .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9739-9745
[4]   Parallel recognition by virtue of differentiation between ketone and aldehyde [J].
Chen, JX ;
Otera, J .
TETRAHEDRON LETTERS, 1998, 39 (13) :1767-1770
[5]   Parallel recognition by virtue of differentiation between carbonyls, acetals and enones [J].
Chen, JX ;
Sakamoto, K ;
Orita, A ;
Otera, J .
TETRAHEDRON, 1998, 54 (29) :8411-8420
[6]   Synthesis and structural characterization of new chiral mixed phosphine phosphoramidite complexes of ruthenium [J].
Costin, Stephen ;
Rath, Nigam P. ;
Bauer, Eike B. .
INORGANICA CHIMICA ACTA, 2009, 362 (06) :1935-1942
[7]  
Doucet H, 2000, SYNLETT, P871
[8]   Catalytic enantioselective Mukaiyama aldol reaction via a chiral indium(III)-pybox complex [J].
Fu, Fan ;
Teo, Yong-Chua ;
Loh, Teck-Peng .
TETRAHEDRON LETTERS, 2006, 47 (25) :4267-4269
[9]   LEWIS ACID MEDIATED ALDOL CONDENSATIONS USING THIOESTER SILYL KETENE ACETALS [J].
GENNARI, C ;
BERETTA, MG ;
BERNARDI, A ;
MORO, G ;
SCOLASTICO, C ;
TODESCHINI, R .
TETRAHEDRON, 1986, 42 (03) :893-909
[10]   Mukaiyama aldol and Michael reactions catalyzed by lanthanide iodides [J].
Giuseppone, N ;
Van de Weghe, P ;
Mellah, M ;
Collin, J .
TETRAHEDRON, 1998, 54 (43) :13129-13148