Stereoselective synthesis of (E)-α,β-unsaturated esters via carbene-catalyzed redox esterification

被引:251
作者
Zeitler, K [1 ]
机构
[1] Univ Regensburg, Inst Organ Chem, D-93053 Regensburg, Germany
关键词
D O I
10.1021/ol052826h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereoselective, carbene-mediated redox esterification of alkynyl aldehydes provides mild and atom economical access to (E)-configurated, alpha,beta-unsaturated carboxylic esters. The organocatalytic method relies on the generation of activated carboxylates via extended/conjugated umpolung in the presence of catalytic amounts of carbene precursor and base.
引用
收藏
页码:637 / 640
页数:4
相关论文
共 52 条
[1]   Rhodium(I)-catalyzed carbonyl allenylation versus propargylation via redox transmetalation across tetragonal tin(II) oxide [J].
Banerjee, M ;
Roy, S .
ORGANIC LETTERS, 2004, 6 (13) :2137-2140
[2]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[3]   The modified Julia olefination:: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds [J].
Blakemore, PR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23) :2563-2585
[4]   RUTHENIUM-CATALYZED ADDITIONS TO ALKYNES - SYNTHESIS OF ACTIVATED ESTERS AND THEIR USE IN ACYLATION REACTIONS [J].
BRUNEAU, C ;
NEVEUX, M ;
KABOUCHE, Z ;
RUPPIN, C ;
DIXNEUF, PH .
SYNLETT, 1991, (11) :755-763
[5]   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
[6]   Conversion of α,β-unsaturated aldehydes into saturated esters:: An umpolung reaction catalyzed by nucleophilic carbenes [J].
Chan, A ;
Scheidt, KA .
ORGANIC LETTERS, 2005, 7 (05) :905-908
[7]  
Chatterjee AK, 2002, ADV SYNTH CATAL, V344, P634, DOI 10.1002/1615-4169(200208)344:6/7<634::AID-ADSC634>3.0.CO
[8]  
2-K
[9]   Direct atom-efficient esterification between carboxylic acids and alcohols catalyzed by amphoteric, water-tolerant TiO(acac)2 [J].
Chen, CT ;
Munot, YS .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21) :8625-8627
[10]   Functionalization of α,β-unsaturated esters and ketones:: A facile and highly stereoselective one-pot approach to N-protected α,β-dehydroamino acid derivatives [J].
Chen, DJ ;
Guo, L ;
Liu, JY ;
Kirtane, S ;
Cannon, JF ;
Li, GG .
ORGANIC LETTERS, 2005, 7 (05) :921-924