Gold-Catalyzed Tandem Cycloisomerization-Halogenation of Chiral Homopropargyl Sulfonamides

被引:22
作者
Shu, Chao [1 ,2 ]
Li, Long [1 ,2 ]
Shen, Cang-Hai [1 ,2 ]
Ruan, Peng-Peng [1 ,2 ]
Liu, Chao-Yue [1 ,2 ]
Ye, Long-Wu [1 ,2 ,3 ]
机构
[1] Xiamen Univ, Coll Chem & Chem Engn, State Key Lab Phys Chem Solid Surfaces, Xiamen 361005, Fujian, Peoples R China
[2] Xiamen Univ, Coll Chem & Chem Engn, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Fujian, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
cycloisomerization; gold; halogenation; heterocycles; homogeneous catalysis; EFFICIENT SYNTHESIS; INTERMOLECULAR OXIDATION; REGIOSELECTIVE SYNTHESIS; TERT-BUTANESULFINAMIDE; ASYMMETRIC-SYNTHESIS; ORGANOGOLD COMPOUNDS; PRACTICAL SYNTHESIS; PROPARGYLIC AMIDES; ALKYNES; DERIVATIVES;
D O I
10.1002/chem.201503891
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Two new gold-catalyzed tandem cycloisomerization-halogenation reactions of chiral homopropargyl sulfonamides have been developed. Various enantioenriched 3,3-diiodopyrrolidin-2-ols and 3-fluoropyrrolidin-2-ols were obtained in moderate-to-good yields with excellent enantio- and diastereoselectivity.
引用
收藏
页码:2282 / 2290
页数:9
相关论文
共 87 条
[21]   Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles [J].
Gulevich, Anton V. ;
Dudnik, Alexander S. ;
Chernyak, Natalia ;
Gevorgyan, Vladimir .
CHEMICAL REVIEWS, 2013, 113 (05) :3084-3213
[22]  
Haro T., 2011, CHEM COMMUN, V47, P248
[23]  
Hashmi A.S. K., 2010, ANGEW CHEM, V122, P5360, DOI DOI 10.1002/ANGE.200907078
[24]  
Hashmi A.S. K., 2009, Angew. Chem, V121, P8396, DOI DOI 10.1002/ANGE.200903134
[25]   Dual Gold Catalysis [J].
Hashmi, A. Stephen K. .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (03) :864-876
[26]   Selectivity Switch in the Synthesis of Vinylgold(I) Intermediates [J].
Hashmi, A. Stephen K. ;
Schuster, Andreas M. ;
Gaillard, Sylvain ;
Cavallo, Luigi ;
Poater, Albert ;
Nolan, Steven P. .
ORGANOMETALLICS, 2011, 30 (22) :6328-6337
[27]   Gold-Catalysis: Reactions of Organogold Compounds with Electrophiles [J].
Hashmi, A. Stephen K. ;
Ramamurthi, Tanuja Dondeti ;
Todd, Matthew H. ;
Tsang, Althea S. -K. ;
Graf, Katharina .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2010, 63 (12) :1619-1626
[28]   Homogeneous Gold Catalysis Beyond Assumptions and Proposals-Characterized Intermediates [J].
Hashmi, A. Stephen K. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (31) :5232-5241
[29]   On the Trapping of Vinylgold Intermediates [J].
Hashmi, A. Stephen K. ;
Ramamurthi, Tanuja Dondeti ;
Rominger, Frank .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (06) :971-975
[30]   Isolable vinylgold intermediates - first access to phantoms of homogeneous gold catalysis [J].
Hashmi, A. Stephen K. .
GOLD BULLETIN, 2009, 42 (04) :275-279