Organocatalytic enantioselective decarboxylative Michael addition of β-ketoacids to α,β-unsaturated ketones

被引：71

作者：

Kang, Young Ku ^{[1
]}

Lee, Hyun Joo ^{[1
]}

Moon, Hyoung Wook ^{[1
]}

Kim, Dae Young ^{[1
]}

机构：

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

来源：

RSC ADVANCES | 2013年 / 3卷 / 05期

关键词：

MANNICH-TYPE REACTIONS; ASYMMETRIC CONJUGATE ADDITION; C-3-SYMMETRIC CHIRAL TRISIMIDAZOLINE; ELECTROPHILIC ALPHA-AMINATION; FRIEDEL-CRAFTS ALKYLATION; ACID HALF-THIOESTERS; QUATERNARY STEREOCENTERS; 1,3-DICARBONYL COMPOUNDS; TERTIARY STEREOCENTERS; POLYKETIDE SYNTHASES;

D O I：

10.1039/c2ra21945j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantioselective decarboxylative Michael addition reactions promoted by chiral primary amine organocatalysts have been developed, allowing the facile synthesis of the corresponding chiral 1,5-diketones with excellent enantioselectivity (up to 97% ee). The method reported represents a valuable approach of utilizing beta-ketoacids as synthetic equivalents of aryl methyl ketones.

引用

页码：1332 / 1335

页数：4

共 106 条

[1] Recent progress in chiral Bronsted acid catalysis [J].

Akiyama, Takahiko ;

Itoh, Junji ;

Fuchibe, Kohei .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010

[2] Organocatalytic asymmetric "anti-Michael" reaction of β-ketoesters [J].

Aleman, Jose ;

Reyes, Efraim ;

Richter, Bo ;

Overgaard, Jacob ;

Jorgensen, Karl Anker .

CHEMICAL COMMUNICATIONS, 2007, (38) :3921-3923

[3] Theory of asymmetric organocatalysis of aldol and related reactions: Rationalizations and predictions [J].

Allemann, C ;

Gordillo, R ;

Clemente, FR ;

Cheong, PHY ;

Houk, KN .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :558-569

[4] Organocatalytic asymmetric conjugate additions [J].

Almasi, Diana ;

Alonso, Diego A. ;

Najera, Carmen .

TETRAHEDRON-ASYMMETRY, 2007, 18 (03) :299-365

[5] 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

[6] Organocatalytic asymmetric conjugate addition of 1,3-dicarbonyl compounds to maleimides [J].

Bartoli, Giuseppe ;

Bosco, Marcella ;

Carlone, Armando ;

Cavalli, Andrea ;

Locatelli, Manuela ;

Mazzanti, Andrea ;

Ricci, Paolo ;

Sambri, Letizia ;

Melchiorre, Paolo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (30) :4966-4970

[7] Organocatalytic Asymmetric Mannich Reactions in the Preparation of Enantio-enriched β3-Amino Acid Derivatives [J].

Bernardi, Luca ;

Ricci, Alfredo ;

Franchini, Mauro Comes .

CURRENT ORGANIC CHEMISTRY, 2011, 15 (13) :2210-2226

[8]

Berner OM, 2002, EUR J ORG CHEM, V2002, P1877

[9] 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

[10] 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

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