N-Heterocyclic Carbene Catalyzed Vinylogous Aldol Reaction of 2-(Trimethylsilyloxy) furan and Aldehydes

被引:26
作者
Du, Guang-Fen [1 ]
He, Lin [1 ]
Gu, Cheng-Zhi [1 ]
Dai, Bin [1 ]
机构
[1] Shi He Zi Univ, Sch Chem & Chem Engn, Xin Jiang 832000, Peoples R China
关键词
N-heterocyclic carbenes; vinylogous aldol reaction; butenolides; 2-(trimethylsilyloxy)furan; aldehyde; HIGHLY ENANTIOSELECTIVE SYNTHESIS; NUCLEOPHILIC CARBENES; EFFICIENT CATALYST; CONJUGATE UMPOLUNG; 4+2 CYCLOADDITION; STETTER REACTION; KETENES; CARBON; CYANOSILYLATION; ACYLATION;
D O I
10.1055/s-0030-1258551
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A N-Heterocyclic carbenes (NHC) catalyzed vinylogous aldol reaction between 2-(trimethylsilyloxy) furan and aldehydes has been developed, providing gamma-substituted butenolides in high yields with good diastereoselectivities. Furthermore, the catalyst loading can be reduced to 1 mol%.
引用
收藏
页码:2513 / 2517
页数:5
相关论文
共 91 条
[21]  
2-Q
[22]   Synthesis of enantiopure triazolium salts from pyroglutamic acid and their evaluation in the benzoin condensation [J].
Enders, Dieter ;
Han, Jianwei .
TETRAHEDRON-ASYMMETRY, 2008, 19 (11) :1367-1371
[23]   Organocatalysis by N-heterocyclic, carbenes [J].
Enders, Dieter ;
Niemeier, Oliver ;
Henseler, Alexander .
CHEMICAL REVIEWS, 2007, 107 (12) :5606-5655
[24]   Concise total synthesis of (-)-muricatacin and (-)-iso-cladospolide B using chemoselective cross-metathesis [J].
Ferrie, Laurent ;
Reymond, Sebastien ;
Capdevielle, Patrice ;
Cossy, Janine .
SYNLETT, 2007, (18) :2891-2893
[25]   Catalyzed Vinylogous Mukaiyama Aldol Reactions with Controlled Enantio- and Diastereoselectivities [J].
Frings, Marcus ;
Atodiresei, Iuliana ;
Runsink, Jan ;
Raabe, Gerhard ;
Bolm, Carsten .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (07) :1566-1569
[26]   Cyano-phosphorylation of aldehydes catalyzed by a nucleophilic N-heterocyclic carbene [J].
Fukuda, Y ;
Maeda, Y ;
Kondo, K ;
Aoyama, T .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (03) :397-398
[27]   An N-heterocyclic carbene as a nucleophilic catalyst for cyanosilylation of aldehydes [J].
Fukuda, Y ;
Maeda, Y ;
Ishii, S ;
Kondo, K ;
Aoyama, T .
SYNTHESIS-STUTTGART, 2006, (04) :589-590
[28]   Construction of tetrasubstituted carbon by an organocatalyst: Cyanation reaction of ketones and ketimines catalyzed by a nucleophilic N-heterocyclic carbene [J].
Fukuda, Yoshimasa ;
Kondo, Kazuhiro ;
Aoyama, Toyohiko .
SYNTHESIS-STUTTGART, 2006, (16) :2649-2652
[29]   Strecker reaction of aldimines catalyzed by a nucleophilic N-heterocyclic carbene [J].
Fukuda, Yoshimasa ;
Maeda, Yuka ;
Kondo, Kazuhiro ;
Aoyama, Toyohiko .
SYNTHESIS-STUTTGART, 2006, 12 (12) :1937-1939
[30]   Neutral Penta- and Hexacoordinate N-Heterocyclic Carbene Complexes Derived from SiX4 (X = F, Br) [J].
Ghadwal, Rajendra S. ;
Sen, Sakya S. ;
Roesky, Herbert W. ;
Tavcar, Gasper ;
Merkel, Sebastian ;
Stalke, Dietmar .
ORGANOMETALLICS, 2009, 28 (21) :6374-6377