Practical asymmetric henry reaction catalyzed by a chiral Diamine-Cu(OAc)2 complex

被引:183
作者
Arai, Takayoshi [1 ]
Watanabe, Masahiko [1 ]
Yanagisawa, Akira [1 ]
机构
[1] Chiba Univ, Grad Sch Sci, Dept Chem, Inage 2638522, Japan
关键词
D O I
10.1021/ol7014362
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The chiral diamine ligand 3 was designed and synthesized from (R,R)-1,2-diphenylethylenediamine, (S)-2,2'-dibromomethyl-1,1'-binaphthalene, and o-xylylene dibromide. The resulting 3-Cu(OAc)(2) complex was a highly efficient catalyst for the Henry reaction, giving the various nitroaldols with over 90% ee (up to > 99%). The reaction was performed in n-propyl alcohol at room temperature, and the Henry adducts were produced in high yield with excellent enantiomeric excess; these attributes are desirable in a catalyst for practical use.
引用
收藏
页码:3595 / 3597
页数:3
相关论文
共 23 条
[1]  
ANASTAS RT, 1998, GREEN CHEM THEORY PR
[2]  
[Anonymous], COMPREHENSIVE ASYMME
[3]   Direct monitoring of the asymmetric induction of solid-phase catalysis using circular dichroism:: Diamine-CuI-catalyzed asymmetric Henry reaction [J].
Arai, Takayoshi ;
Watanabe, Masahiko ;
Fujiwara, Akitsugu ;
Yokoyama, Naota ;
Yanagisawa, Akira .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (36) :5978-5981
[4]   Recoverable PEG-supported copper catalyst for highly stereocontrolled nitroaldol condensation [J].
Bandini, Marco ;
Benaglia, Maurizio ;
Sinisi, Riccardo ;
Tommasi, Simona ;
Umani-Ronchi, Achille .
ORGANIC LETTERS, 2007, 9 (11) :2151-2153
[5]   Nanocrystalline MgO for asymmetric Henry and Michael reactions [J].
Choudary, BM ;
Ranganath, KVS ;
Pal, U ;
Kantam, ML ;
Sreedhar, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) :13167-13171
[6]   Catalytic asymmetric Henry reactions -: a simple approach to optically active β-nitro α-hydroxy esters [J].
Christensen, C ;
Juhl, K ;
Jorgensen, KA .
CHEMICAL COMMUNICATIONS, 2001, (21) :2222-2223
[7]   A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction [J].
Evans, DA ;
Seidel, D ;
Rueping, M ;
Lam, HW ;
Shaw, JT ;
Downey, CW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) :12692-12693
[8]   Asymmetric catalysis in the pharmaceutical industry [J].
Hawkins, JM ;
Watson, TJN .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (25) :3224-3228
[9]   Enantioselective Henry reaction catalyzed by optically active ketoiminatocobalt complexes [J].
Kogami, Y ;
Nakajima, T ;
Ashizawa, T ;
Kezuka, S ;
Ikeno, T ;
Yamada, T .
CHEMISTRY LETTERS, 2004, 33 (05) :614-615
[10]  
MA K, 2007, CHEM COMMUN, P616