Organocatalysis in Enantioselective α-Functionalization of 2-Cyanoacetates

被引:24
作者
Diaz-de-Villegas, Maria D. [1 ]
Galvez, Jose A. [1 ]
Badorrey, Ramon [1 ]
Lopez-Ram-de-Viu, Pilar [1 ]
机构
[1] Univ Zaragoza, CSIC, ISQCH, Dept Catalisis & Proc Catalit, E-50009 Zaragoza, Spain
关键词
cyanides; cyano esters; enantioselectivity; organic catalysis; synthetic methods; ASYMMETRIC CONJUGATE ADDITION; PINCER PALLADIUM COMPLEXES; PHASE-TRANSFER; SUBSTITUTED CYANOACETATES; MICHAEL ADDITION; MULTICOMPONENT REACTIONS; ALLYLIC ALKYLATION; ALPHA; BETA-UNSATURATED IMIDES; STEREOSELECTIVE AMINATION; QUATERNARY STEREOCENTERS;
D O I
10.1002/adsc.201400404
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Recent progress in asymmetric organocatalysis has led to the development of several asymmetric transformations that employ various substrates. Among these, cyanoacetates have emerged as excellent nucleophiles in conjugate addition, alkylation, Mannich and alpha-heterofunctionalization reactions. In this review we discuss the enantioselective functionalization of 2-cyanoacetates through organocatalytic reactions.
引用
收藏
页码:3261 / 3288
页数:28
相关论文
共 132 条
[1]   First asymmetric synthesis of an acyclic β,β-dialkylated-γ-aminobutyric acid [J].
Aguirre, Daniel ;
Cativiela, Carlos ;
Diaz-de-Villegas, Maria D. ;
Galvez, Jose A. .
TETRAHEDRON, 2006, 62 (34) :8142-8146
[2]   Organocatalytic Asymmetric Synthesis of Organophosphorus Compounds [J].
Albrecht, Lukasz ;
Albrecht, Anna ;
Krawczyk, Henryk ;
Jorgensen, Karl Anker .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (01) :28-48
[3]   Applications of asymmetric organocatalysis in medicinal chemistry [J].
Aleman, Jose ;
Cabrera, Silvia .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (02) :774-793
[4]   Organocatalytic asymmetric conjugate additions [J].
Almasi, Diana ;
Alonso, Diego A. ;
Najera, Carmen .
TETRAHEDRON-ASYMMETRY, 2007, 18 (03) :299-365
[5]  
[Anonymous], ANGEW CHEM
[6]   Efficient enantioconvergent synthesis of (S)-α-benzyl-α-methyl-β-alanine from (R)- and (S)-2-cyano-2-methyl-3-phenylpropanoic acid [J].
Badorrey, R ;
Cativiela, C ;
Díaz-De-Villegas, MD ;
Gálvez, JA ;
Gil, A .
TETRAHEDRON-ASYMMETRY, 2003, 14 (15) :2209-2214
[7]   STEREOSELECTIVE AMINATION OF CHIRAL ENOLATES - SYNTHESIS OF ENANTIOMERICALLY PURE ALPHA,BETA-DIAMINO ACIDS, CHIRAL KEY COMPOUNDS IN THE SYNTHESIS OF CONFORMATIONALLY CONSTRAINED PEPTIDOMIMETRICS AND NON-PEPTIDOMIMETICS [J].
BADORREY, R ;
CATIVIELA, C ;
DIAZDEVILLEGAS, MD ;
GALVEZ, JA .
TETRAHEDRON-ASYMMETRY, 1995, 6 (11) :2787-2796
[8]   α,β-unsaturated β-silyl imide substrates for catalytic, enantioselective conjugate additions:: A total synthesis of (+)-lactacystin and the discovery of a new proteasome inhibitor [J].
Balskus, Emily P. ;
Jacobsen, Eric N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6810-6812
[9]   Organocatalytic enantioselective nucleophilic vinylic substitution by α-substituted-α-cyanoacetates under phase-transfer conditions [J].
Bell, Mark ;
Poulsen, Thomas B. ;
Jorgensen, Karl Anker .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (08) :3053-3056
[10]   Recent advances in multicomponent reactions for diversity-oriented synthesis [J].
Biggs-Houck, James E. ;
Younai, Ashkaan ;
Shaw, Jared T. .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2010, 14 (03) :371-382