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
[1]   Annonaceous acetogenins: Recent progress [J].
Alali, FQ ;
Liu, XX ;
McLaughlin, JL .
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (03) :504-540
[2]   A STABLE CRYSTALLINE CARBENE [J].
ARDUENGO, AJ ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363
[3]   Imidazolylidenes, imidazolinylidenes and imidazolidines [J].
Arduengo, AJ ;
Krafczyk, R ;
Schmutzler, R ;
Craig, HA ;
Goerlich, JR ;
Marshall, WJ ;
Unverzagt, M .
TETRAHEDRON, 1999, 55 (51) :14523-14534
[4]   TRANSFER OF ALKOXYCARBONYL FROM ALKYL IMIDAZOLIUM-2-CARBOXYLATES TO BENZYL ALCOHOL, A CYCLOHEXANONE ENAMINE AND DIETHYLAMINE [J].
BAKHTIAR, C ;
SMITH, EH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (03) :239-243
[5]   Highly stereoselective addition of 2-trimethylsilyloxyfuran to N-glyoxyloyl-(2R)-bornane-10,2-sultam [J].
Bauer, T .
TETRAHEDRON-ASYMMETRY, 1996, 7 (04) :981-984
[6]   N-Heterocyclic Carbene-Catalyzed Cascade Reaction Involving the Hydroacylation of Unactivated Alkynes [J].
Biju, Akkattu T. ;
Wurz, Nathalie E. ;
Glorius, Frank .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (17) :5970-+
[7]   REGIOSTEREOSELECTIVITY AND DIASTEREOSELECTIVITY IN ALDOL REACTIONS OF CYCLOPENT-2-ENONE, 2-(5H)FURANONE AND THEIR DERIVED TRIMETHYLSILYLOXYDIENES [J].
BROWN, DW ;
CAMPBELL, MM ;
TAYLOR, AP ;
ZHANG, X .
TETRAHEDRON LETTERS, 1987, 28 (09) :985-988
[8]   Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones [J].
Burstein, C ;
Glorius, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) :6205-6208
[9]   N-heterocyclic carbene-catalyzed conjugate umpolung for the synthesis of γ-butyrolactones [J].
Burstein, Christian ;
Tschan, Serena ;
Xie, Xiulan ;
Glorius, Frank .
SYNTHESIS-STUTTGART, 2006, (14) :2418-2439
[10]   The vinylogous aldol reaction: A valuable, yet understated carbon-carbon bond-forming maneuver [J].
Casiraghi, G ;
Zanardi, F ;
Appendino, G ;
Rassu, G .
CHEMICAL REVIEWS, 2000, 100 (06) :1929-1972