Assembly of Spirooxindole Derivatives Containing Four Consecutive Stereocenters by Using Cascade Reactions Catalyzed by an N-Heterocyclic Carbene

被引：53

作者：

Zhou, Bing ^{[1
]}

Luo, Zhi ^{[1
]}

Li, Yuanchao ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 14期

关键词：

carbenes; domino reactions; oxindoles; redox chemistry; spiro compounds; DIELS-ALDER REACTIONS; ASYMMETRIC TOTAL-SYNTHESIS; PICTET-SPENGLER REACTIONS; SPIROCYCLIC OXINDOLES; ALPHA; BETA-UNSATURATED ALDEHYDES; ENANTIOSELECTIVE CONSTRUCTION; ALKYNYL ALDEHYDES; NATURAL-PRODUCTS; 3+2 ANNULATION; EFFICIENT;

D O I：

10.1002/chem.201203436

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In-spiro-ational: Biologically important and synthetically challenging spirocyclopentaneoxindoles with four consecutive stereocenters, including one spiroquaternary stereocenter, have been constructed in good yields and diastereoselectivity by a cascade reaction catalyzed by an N-heterocyclic carbene (see scheme). This reaction also provides a new strategy to access highly unusual tricyclic oxindoles. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：4428 / 4431

页数：4

共 77 条

[1] Assembly of Spirooxindole Derivatives Containing Four Consecutive Stereocenters via Organocatalytic Michael-Henry Cascade Reactions [J].

Albertshofer, Klaus ;

Tan, Bin ;

Barbas, Carlos F., III .

ORGANIC LETTERS, 2012, 14 (07) :1834-1837

[2] Oxyanion Steering and CH-π Interactions as Key Elements in an N-Heterocyclic Carbene-Catalyzed [4+2] Cycloaddition [J].

Allen, Scott E. ;

Mahatthananchai, Jessada ;

Bode, Jeffrey W. ;

Kozlowski, Marisa C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (29) :12098-12103

[3]

[Anonymous], 2007, ANGEW CHEM, DOI DOI 10.1103/PHYSREVLETT.112.077206

[4] Catalytic Asymmetric exo'-Selective [3+2] Cycloaddition for Constructing Stereochemically Diversified Spiro[pyrrolidin-3,3'-oxindole]s [J].

Awata, Atsuko ;

Arai, Takayoshi .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (27) :8278-8282

[5] 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

[6]

Bencivenni G., 2009, ANGEW CHEM, V121, P7336

[7] Targeting Structural and Stereochemical Complexity by Organocascade Catalysis: Construction of Spirocyclic Oxindoles Having Multiple Stereocenters [J].

Bencivenni, Giorgio ;

Wu, Li-Yuan ;

Mazzanti, Andrea ;

Giannichi, Berardino ;

Pesciaioli, Fabio ;

Song, Mao-Ping ;

Bartoli, Giuseppe ;

Melchiorre, Paolo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (39) :7200-7203

[8] Extending NHC-Catalysis: Coupling Aldehydes with Unconventional Reaction Partners [J].

Biju, Akkattu T. ;

Kuhl, Nadine ;

Glorius, Frank .

ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (11) :1182-1195

[9] CYCLOPIAMINES-A AND CYCLOPIAMINES-B NOVEL OXINDOLE METABOLITES OF PENICILLIUM-CYCLOPIUM WESTLING [J].

BOND, RF ;

BOEYENS, JCA ;

HOLZAPFEL, CW ;

STEYN, PS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (07) :1751-1761

[10]

Cao Y.-M., 2011, ANGEW CHEM, V123, P9290, DOI DOI 10.1002/ANGE.201104216

← 1 2 3 4 5 6 7 8 →