An Organocatalysis Based Carbocyclic Spiroindoline Synthesis Enables Facile Structure-Activity Relationship (SAR) Study at C2 Position

被引：12

作者：

Zheng, Yongsheng ^{[1
]}

Cleaveland, Jacob ^{[1
]}

Richardson, David ^{[1
]}

Yuan, Yu ^{[1
]}

机构：

[1] Univ Cent Florida, Dept Chem, Orlando, FL 32816 USA

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 17期

关键词：

ENANTIOSELECTIVE CONSTRUCTION; SPIROCYCLOPENTANE BIOXINDOLES; CONTIGUOUS STEREOCENTERS; SPIROCYCLIC OXINDOLES; MICHAEL ADDITIONS; NATURAL-PRODUCTS; CASCADE; DERIVATIVES; ALDEHYDES; INDOLINE;

D O I：

10.1021/acs.orglett.5b02031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric synthesis of carbocyclic spiroindoline by sequential Michael reaction and [3 + 2]-cycloaddition is described. This protocol demonstrates excellent enantio- and diastereoselectivity with broad functional group tolerance. A diverse range of spiroindolines were prepared by this approach, and the products served as ideal substrates for C2 derivatization.

引用

页码：4240 / 4243

页数：4

共 43 条

[1] Asymmetric Organocatalysis and the Nitro Group Functionality [J].

Aitken, Lewis S. ;

Arezki, Natasha R. ;

Dell'Isola, Antonio ;

Cobb, Alexander J. A. .

SYNTHESIS-STUTTGART, 2013, 45 (19) :2627-2648

[2] 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

[3]

[Anonymous], THE NITRILE OXIDES

[4] Efficient Recovery and Reuse of an Immobilized Peptidic Organocatalyst [J].

Arakawa, Yukihiro ;

Wiesner, Markus ;

Wennemers, Helma .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (08) :1201-1206

[5] Catalytic Enantioselective Carboannulation with Allylsilanes [J].

Ball-Jones, Nicolas R. ;

Badillo, Joseph J. ;

Tran, Ngon T. ;

Franz, Annaliese K. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (36) :9462-9465

[6]

Basel Y, 1997, SYNTHESIS-STUTTGART, P309

[7] Synthesis of strychnine [J].

Bonjoch, J ;

Solé, D .

CHEMICAL REVIEWS, 2000, 100 (09) :3455-3482

[8] Sequential Organocatalyzed Michael Addition/[3+2]-Heterocyclization for the Stereoselective Synthesis of Fused-Isoxazoline Precursors of Enantiopure Cyclopentanoids [J].

Bonne, Damien ;

Salat, Lydie ;

Dulcere, Jean-Pierre ;

Rodriguez, Jean .

ORGANIC LETTERS, 2008, 10 (23) :5409-5412

[9] Enantioselective Gold-Catalyzed Synthesis of Polycyclic Indolines [J].

Cera, Gianpiero ;

Chiarucci, Michel ;

Mazzanti, Andrea ;

Mancinelli, Michele ;

Bandini, Marco .

ORGANIC LETTERS, 2012, 14 (05) :1350-1353

[10] Design, synthesis, and SAR of new pyrrole-oxindole progesterone receptor modulators leading to 5-(7-Fluoro-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrrole-2-carbonitrile (WAY-255348) [J].

Fensome, Andrew ;

Adams, William R. ;

Adams, Andrea L. ;

Berrodin, Tom J. ;

Cohen, Jeff ;

Huselton, Christine ;

Illenberger, Arthur ;

Kern, Jeffrey C. ;

Hudak, Valerie A. ;

Marella, Michael A. ;

Melenski, Edward G. ;

McComas, Casey C. ;

Mugford, Cheryl A. ;

Slayden, Ov D. ;

Yudt, Matthew ;

Zhang, Zhiming ;

Zhang, Puwen ;

Zhu, Yuan ;

Winneker, Richard C. ;

Wrobel, Jay E. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (06) :1861-1873

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