Asymmetric Allylic Alkylation of Isatin-Derived Morita-Baylis-Hillman Carbonates with Nitroalkanes

被引:50
作者
Chen, Guo-Ying
Zhong, Fangrui
Lu, Yixin [1 ]
机构
[1] Natl Univ Singapore, Inst Life Sci, Dept Chem, Singapore 117543, Singapore
关键词
CONJUGATE ADDITION-ELIMINATION; ENANTIOSELECTIVE CONSTRUCTION; QUATERNARY STEREOCENTERS; PHOSPHINES SYNTHESIS; OXINDOLE ALKALOIDS; ACID-DERIVATIVES; SUBSTITUTION; ACETATES; CENTERS; HYDROGENATION;
D O I
10.1021/ol301962e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A stereoselective allylic alkylation of isatin-derived Morita-Baylis-Hillman (MBH) carbonates with nitroalkanes has been developed. In the presence of 10 mol % beta-isocupreidine (beta-ICD), 3,3'-disubstituted oxindoles were prepared with moderate diastereoselectivities and excellent enantioselectivities.
引用
收藏
页码:3955 / 3957
页数:3
相关论文
共 53 条
[1]   Oxindoles from Phalaris coerulescens [J].
Anderton, N ;
Cockrum, PA ;
Colegate, SM ;
Edgar, JA ;
Flower, K ;
Vit, I ;
Willing, RI .
PHYTOCHEMISTRY, 1998, 48 (03) :437-439
[2]  
[Anonymous], 2009, Curr. Bioact. Compd., DOI [10.2174/157340709787580900, DOI 10.2174/157340709787580900]
[3]   Asymmetric synthesis of 2-alkyl-3-phosphonopropanoic acids via p-c bond formation and hydrogenation [J].
Badkar, Pallavi A. ;
Rath, Nigam P. ;
Spilling, Christopher D. .
ORGANIC LETTERS, 2007, 9 (18) :3619-3622
[4]   Applications of Baylis-Hillman acetates:: one-pot, facile and convenient synthesis of substituted γ-lactams [J].
Basavaiah, D ;
Rao, JS .
TETRAHEDRON LETTERS, 2004, 45 (08) :1621-1625
[5]   Organocatalytic Formation of Quaternary Stereocenters [J].
Bella, Marco ;
Gasperi, Tecla .
SYNTHESIS-STUTTGART, 2009, (10) :1583-1614
[6]   Dimeric Quinidine-Catalyzed Enantioselective Aminooxygenation of Oxindoles: An Organocatalytic Approach to 3-Hydroxyoxindole Derivatives [J].
Bui, Tommy ;
Candeias, Nuno R. ;
Barbas, Carlos F., III .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (16) :5574-+
[7]   Highly Enantioselective Cu-Catalyzed Conjugate Addition-Elimination of Activated Allylic Acetates with Glycine Derivatives [J].
Chen, Chun-Gen ;
Hou, Xue-Long ;
Pu, Lin .
ORGANIC LETTERS, 2009, 11 (10) :2073-2075
[8]   Highly Enantioselective and Regioselective Substitution of Morita-Baylis-Hillman Carbonates with Nitroalkanes [J].
Chen, Guo-Ying ;
Zhong, Fangrui ;
Lu, Yixin .
ORGANIC LETTERS, 2011, 13 (22) :6070-6073
[9]  
Christoffers J, 2005, QUATERNARY STEREOCENTERS: CHALLENGES AND SOLUTIONS FOR ORGANIC SYNTHESIS, P1, DOI 10.1002/3527606858
[10]   Enantioselective catalytic formation of quaternary stereogenic centers [J].
Cozzi, Pier Giorgio ;
Hilgraf, Robert ;
Zimmermann, Nicole .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (36) :5969-5994