Enantioselective Synthesis of AG-041R by using N-Heteroarenesulfonyl Cinchona Alkaloid Amides as Organocatalysts

被引：196

作者：

Hara, Noriyuki ^{[1
]}

Nakamura, Shuichi ^{[1
]}

Sano, Masahide ^{[1
]}

Tamura, Ryota ^{[1
]}

Funahashi, Yasuhiro ^{[1
]}

Shibata, Norio ^{[1
]}

机构：

[1] Nagoya Inst Technol, Dept Frontier Mat, Grad Sch Engn, Showa Ku, Nagoya, Aichi 4668555, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 30期

基金：

日本科学技术振兴机构;

关键词：

enantioselectivity; ketimines; organocatalysis; reaction mechanisms; ASYMMETRIC MANNICH REACTION; PICTET-SPENGLER REACTIONS; QUATERNARY CARBON CENTER; ACID HALF-THIOESTERS; ALPHA-AMINATION; DECARBOXYLATIVE ADDITION; POLYKETIDE SYNTHASES; RECEPTOR ANTAGONISTS; MICHAEL-ADDITION; KETIMINES;

D O I：

10.1002/chem.201200367

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The organocatalytic enantioselective decarboxylative addition of malonic acid half thioesters to ketimines derived from isatins by using N-heteroarenesulfonyl cinchona alkaloid amides afforded products with high enantioselectivity. The products could be converted into optically active AG-041R. X-ray crystallographic analysis revealed that the hydrogen bonding between the sulfonimide proton and the 8-quinolyl nitrogen atom plays an important role in exerting the enantioselectivity of the reaction.

引用

页码：9276 / 9280

页数：5

共 74 条

[1]

[Anonymous], 2011, ANGEW CHEM

[2]

[Anonymous], 2011, ANGEW CHEM

[3] Enantioselective Pictet-Spengler reactions of isatins for the synthesis of spiroindolones [J].

Badillo, Joseph J. ;

Silva-Garcia, Abel ;

Shupe, Benjamin H. ;

Fettinger, James C. ;

Franz, Annaliese K. .

TETRAHEDRON LETTERS, 2011, 52 (43) :5550-5553

[4] 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

[5] Highly enantioselective organocatalytic formation of a quaternary carbon center via chiral Bronsted acid catalyzed self-coupling of enamides [J].

Baudequin, Christine ;

Zamfir, Alexandru ;

Tsogoeva, Svetlana B. .

CHEMICAL COMMUNICATIONS, 2008, (38) :4637-4639

[6]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

[7] Highly Enantioselective Organocatalytic α-Amination Reactions of Aryl Oxindoles: Developing Designer Multifunctional Alkaloid Catalysts [J].

Bui, Tommy ;

Hernandez-Torres, Gloria ;

Milite, Ciro ;

Barbas, Carlos F., III .

ORGANIC LETTERS, 2010, 12 (24) :5696-5699

[8] Expanding the Scope of Cinchona Alkaloid-Catalyzed Enantioselective α-Aminations of Oxindoles: A Versatile Approach to Optically Active 3-Amino-2-oxindole Derivatives [J].

Bui, Tommy ;

Borregan, Mar ;

Barbas, Carlos F., III .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (23) :8935-8938

[9] Highly Enantioselective and Organocatalytic α-Amination of 2-Oxindoles [J].

Cheng, Liang ;

Liu, Li ;

Wang, Dong ;

Chen, Yong-Jun .

ORGANIC LETTERS, 2009, 11 (17) :3874-3877

[10]

Chiba T, 1998, YALE J BIOL MED, V71, P247

← 1 2 3 4 5 6 7 8 →