Highly diastereoselective reactions of 2-lithiated indoles with chiral N-tert-butanesulfinyl aldimines for the synthesis of chiral (2-indolyl) methanamine derivatives

被引:24
作者
Cheng, Liang
Liu, Li [1 ]
Sui, Yong
Wang, Dong
Chen, Yong-Jun
机构
[1] Chinese Acad Sci, Inst Chem, Biol Chem Lab, Beijing Natl Lab Mol Sci, Beijing 100080, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/j.tetasy.2007.07.029
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Nucleophilic addition reactions of 2-lithiated N-phenylsulfonylindoles with (R)-N-tert-butanesulfinyl aldimines provided chiral (2-indolyl) methanamine derivatives in moderate to good yields (up to 100%) with excellent diastereoselectivities (>99: 1), in which no additional Lewis acids were required. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1833 / 1843
页数:11
相关论文
共 46 条
[31]   MODULATION OF THE ANTITUMOR-ACTIVITY BY METHYL SUBSTITUTIONS IN THE SERIES OF 7H-PYRIDOCARBAZOLE MONOMERS AND DIMERS [J].
LEON, P ;
GARBAYJAUREGUIBERRY, C ;
BARSI, MC ;
LEPECQ, JB ;
ROQUES, BP .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (11) :2074-2080
[32]   PREPARATION OF 1-ARYL-BETA-CARBOLINES [J].
LOVE, BE ;
RAJE, PS .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :3219-3222
[33]   Total synthesis of novel subclass of glyco-amino acid structure motif:: C2-α-L-C-mannosylpyranosyl-L-tryptophan [J].
Manabe, S ;
Ito, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) :9754-9755
[34]  
Modi S. P., 1970, J CHEM SOC CHEM COMM, P1095
[35]   Chiral non-racemic sulfinimines: versatile reagents for asymmetric synthesis [J].
Morton, Daniel ;
Stockman, Robert A. .
TETRAHEDRON, 2006, 62 (38) :8869-8905
[36]  
Senanayake CH, 2005, ALDRICHIM ACTA, V38, P93
[37]  
Sundberg R.J., 1996, INDOLES
[38]  
Sundberg R.J., 1970, CHEM INDOLES
[39]   SYNTHESES WITH N-PROTECTED 2-LITHIOINDOLES [J].
SUNDBERG, RJ ;
RUSSELL, HF .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (19) :3324-3330
[40]   Development of a catalytic electron transfer system mediated by transition metal ate complexes: Applicability and tunability of electron-releasing potential for organic transformations [J].
Uchiyama, M ;
Matsumoto, Y ;
Nakamura, S ;
Ohwada, T ;
Kobayashi, N ;
Yamashita, N ;
Matsumiya, A ;
Sakamoto, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (28) :8755-8759