N-heterocyclic carbene-catalyzed conjugate umpolung for the synthesis of γ-butyrolactones

被引：176

作者：

Burstein, Christian ^{[1
]}

Tschan, Serena ^{[1
]}

Xie, Xiulan ^{[1
]}

Glorius, Frank ^{[1
]}

机构：

[1] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany

来源：

SYNTHESIS-STUTTGART | 2006年 / 14期

关键词：

carbenes; Umpolung; lactones; heterocycles; cyclization;

D O I：

10.1055/s-2006-942447

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The N-heterocyclic carbene-catalyzed conjugate Umpolung of differently substituted alpha,beta-unsaturated aldehydes, e.g. cinnamaldehydes, alpha-methylcinnamaldehydes, and crotonaldehydes, is described. Coupling of these compounds with a variety of electro- philic aldehydes and ketones results in the selective formation of highly substituted beta- and gamma-butyrolactones.

引用

页码：2418 / 2439

页数：22

共 88 条

[1] Ahlbrecht H, 1999, SYNTHESIS-STUTTGART, P365
[2] Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis
Altenhoff, G
Goddard, R
Lehmann, CW
Glorius, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) : 15195 - 15201
[3] An N-heterocyclic carbene ligand with flexible steric bulk allows Suzuki cross-coupling of sterically hindered aryl chlorides at room temperature
Altenhoff, G
Goddard, R
Lehmann, CW
Glorius, F
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) : 3690 - 3693
[4] The quest for stable carbenes
Arduengo, AJ
Krafczyk, R
[J]. CHEMIE IN UNSERER ZEIT, 1998, 32 (01) : 6 - 14
[5] An efficient palladium-catalyzed synthesis of cinnamaldehydes from acrolein diethyl acetal and aryl iodides and bromides
Battistuzzi, G
Cacchi, S
Fabrizi, G
[J]. ORGANIC LETTERS, 2003, 5 (05) : 777 - 780
[6] Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[7] Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot Sila-Stetter/Paal-Knorr strategy
Bharadwaj, AR
Scheidt, KA
[J]. ORGANIC LETTERS, 2004, 6 (14) : 2465 - 2468
[8] SYNTHESIS OF KETONES OF TYPE CH3COCH2R FROM ACETYLACETONE AND HALIDES WITH ETHANOLIC POTASSIUM CARBONATE . AN ALKYLATION-CLEAVAGE PROCESS
BOATMAN, S
HARRIS, TM
HAUSER, CR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (10) : 3321 - &
[9] Stable carbenes
Bourissou, D
Guerret, O
Gabbaï, FP
Bertrand, G
[J]. CHEMICAL REVIEWS, 2000, 100 (01) : 39 - 91
[10] A novel one-pot pyrrole synthesis via a coupling-isomerization-Stetter-Paal-knorr sequence
Braun, RU
Zeitler, K
Muller, TJJ
[J]. ORGANIC LETTERS, 2001, 3 (21) : 3297 - 3300

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