Enantioselective decarboxylative aldol addition of β-ketoacids to isatins catalyzed by binaphthyl-modified organocatalyst

被引：74

作者：

Suh, Chang Won ^{[1
]}

Chang, Chul Woo ^{[1
]}

Choi, Keon Woong ^{[1
]}

Lim, Young Jo ^{[1
]}

Kim, Dae Young ^{[1
]}

机构：

[1] Soonchunhyang Univ, Dept Chem, Asan 336745, Chungnam, South Korea

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 28期

关键词：

Asymmetric catalysis; Organocatalysis; Aldol addition; 3-Hydroxy oxindole; Isatins; beta-Ketoacids; MANNICH-TYPE REACTIONS; ASYMMETRIC CONJUGATE ADDITION; FRIEDEL-CRAFTS ALKYLATION; ACID HALF-THIOESTERS; MICHAEL-ADDITION; KETO-ESTERS; STEREOSELECTIVE-SYNTHESIS; POLYKETIDE SYNTHASES; UNACTIVATED KETONES; ALPHA-NITROACETATE;

D O I：

10.1016/j.tetlet.2013.04.132

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic enantioselective decarboxylative aldol addition reaction of isatins with beta-ketoacids promoted by chiral bifunctional organocatalysts have been developed, allowing facile synthesis of the corresponding chiral 3-hydroxy-3-phenacyloxindole derivatives with excellent enantioselectivity (up to 97% ee). (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：3651 / 3654

页数：4

共 76 条

[1] Enantioselective organocatalytic aldol reaction of unactivated ketones with isatins [J].

Allu, Suresh ;

Molleti, Nagaraju ;

Panem, Ramachandrarao ;

Singh, Vinod K. .

TETRAHEDRON LETTERS, 2011, 52 (32) :4080-4083

[2] Water influences the enantioselectivity in the proline or prolinamide-catalyzed aldol addition of acetone to isatins [J].

Angelici, Gaetano ;

Correa, Rodrigo J. ;

Garden, Simon J. ;

Tomasini, Claudia .

TETRAHEDRON LETTERS, 2009, 50 (07) :814-817

[3] Organocatalytic Enantioselective Michael-Addition of Malonic Acid Half-Thioesters to β-Nitroolefins: From Mimicry of Polyketide Synthases to Scalable Synthesis of γ-Amino Acids [J].

Bae, Han Yong ;

Some, Surajit ;

Lee, Jae Heon ;

Kim, Ju-Young ;

Song, Myoung Jong ;

Lee, Sungyul ;

Zhang, Yong Jian ;

Song, Choong Eui .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (17) :3196-3202

[4] Asymmetric Malonic and Acetoacetic Acid Syntheses - A Century of Enantioselective Decarboxylative Protonations [J].

Blanchet, Jerome ;

Baudoux, Jerome ;

Amere, Mukkanti ;

Lasne, Marie-Claire ;

Rouden, Jacques .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (33) :5493-5506

[5] Decarboxylative Ketone Aldol Reactions: Development and Mechanistic Evaluation under Metal-Free Conditions [J].

Blaquiere, Nicole ;

Shore, Daniel G. ;

Rousseaux, Sophie ;

Fagnou, Keith .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16) :6190-6198

[6] L-proline-catalyzed asymmetric aldol condensation of N-substituted isatins with acetone [J].

Chen, Gang ;

Wang, Ye ;

He, Hongping ;

Gao, Suo ;

Yang, Xiaosheng ;

Hao, Xiaojiang .

HETEROCYCLES, 2006, 68 (11) :2327-2333

[7] Organocatalytic asymmetric aldol reaction of ketones with isatins: straightforward stereoselective synthesis of 3-alkyl-3-hydroxyindolin-2-ones [J].

Chen, Jia-Rong ;

Liu, Xiao-Peng ;

Zhu, Xiao-Yu ;

Li, Liang ;

Qiao, Yong-Feng ;

Zhang, Jian-Ming ;

Xiao, Wen-Jing .

TETRAHEDRON, 2007, 63 (42) :10437-10444

[8] Highly enantioselective aldol reaction of acetaldehyde and isatins only with 4-hydroxydiarylprolinol as catalyst: concise stereoselective synthesis of (R)-convolutamydines B and E, (-)-donaxaridine and (R)-chimonamidine [J].

Chen, Wen-Bing ;

Du, Xi-Lin ;

Cun, Lin-Feng ;

Zhang, Xiao-Mei ;

Yuan, Wei-Cheng .

TETRAHEDRON, 2010, 66 (07) :1441-1446

[9] Catalyst-free aldol condensation of ketones and isatins under mild reaction conditions in DMF with molecular sieves 4 Å as additive [J].

Chen, Wen-Bing ;

Liao, Yu-Hua ;

Du, Xi-Lin ;

Zhang, Xiao-Mei ;

Yuan, Wei-Cheng .

GREEN CHEMISTRY, 2009, 11 (09) :1465-1476

[10] Stereoelectronic effects dictate mechanistic dichotomy between Cu(II)-catalyzed and enzyme-catalyzed reactions of malonic acid half thioesters [J].

Fortner, Kevin C. ;

Shair, Matthew D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (05) :1032-1033

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