Enantioselective Nitroso Aldol Reaction Catalyzed by QuinoxP*•Silver(I) Complex and Tin Methoxide

被引:61
作者
Yanagisawa, Akira [1 ]
Takeshita, Satoshi [1 ]
Izumi, Youhei [1 ]
Yoshida, Kazuhiro [1 ]
机构
[1] Chiba Univ, Grad Sch Sci, Dept Chem, Chiba 2638522, Japan
关键词
ASYMMETRIC ALPHA-AMINOXYLATION; ALDEHYDES; KETONES; 1,2-DIOLS; HYDROXY; LIGAND; RICH;
D O I
10.1021/ja910588w
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A catalytic enantioselective O-nitroso aldol reaction of alkenyl trichloroacetates with nitrosoarenes was achieved using the (R,R)-t-Bu-QuinoxP*center dot AgOAc complex as the chiral catalyst and Bu(2)Sn(OMe)(2) as the achiral cocatalyst in the presence of methanol. Optically active a-aminooxy ketones with up to 99% ee were regioselectively obtained in high yields from various alkenyl trichloroacetates of cyclic ketones.
引用
收藏
页码:5328 / +
页数:3
相关论文
共 24 条
[1]   Direct catalytic enantioselective α-aminoxylation of ketones:: A stereoselective synthesis of α-hydroxy and α,α′-dihydroxy ketones [J].
Bogevig, A ;
Sundén, H ;
Córdova, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) :1109-1112
[2]   The direct and enantioselective organocatalytic α-oxidation of aldehydes [J].
Brown, SP ;
Brochu, MP ;
Sinz, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10808-10809
[3]   Direct proline-catalyzed asymmetric α-aminoxylation of ketones [J].
Hayashi, Y ;
Yamaguchi, J ;
Sumiya, T ;
Shoji, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) :1112-1115
[4]   Highly enantioselective hydrosilylation of simple ketones catalyzed by rhodium complexes of P-chiral diphosphine ligands bearing tert-butylmethylphosphino groups [J].
Imamoto, T ;
Itoh, T ;
Yamanoi, Y ;
Narui, R ;
Yoshida, K .
TETRAHEDRON-ASYMMETRY, 2006, 17 (04) :560-565
[5]   An air-stable P-chiral phosphine ligand for highly enantioselective transition-metal-catalyzed reactions [J].
Imamoto, T ;
Sugita, K ;
Yoshida, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (34) :11934-11935
[6]   t-Bu-QuinoxP* ligand: Applications in asymmetric pd-catalyzed allylic substitution and Ru-catalyzed hydrogenation [J].
Imamoto, Tsuneo ;
Nishimura, Miwako ;
Koide, Aya ;
Yoshida, Kazuhiro .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19) :7413-7416
[7]   Recent advances in catalytic, enantioselective α aminations and α oxygenations of carbonyl compounds [J].
Janey, JM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (28) :4292-4300
[8]   A Sequential O-Nitrosoaldol and Grignard Addition Process: An Enantio- and Diastereoselective Entry to Chiral 1,2-Diols [J].
Jiao, Peng ;
Kawasaki, Masanori ;
Yamamoto, Hisashi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (18) :3333-3336
[9]   Direct asymmetric hydroxyamination reaction catalyzed by an axially chiral secondary amine catalyst [J].
Kano, Taichi ;
Ueda, Mitsuhiro ;
Takai, Jun ;
Maruoka, Keiji .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (18) :6046-6047
[10]   Enantioselectivity Switch in Direct Asymmetric Aminoxylation Catalyzed by Binaphthyl-Based Chiral Secondary Amines [J].
Kano, Taichi ;
Yamamoto, Akihiro ;
Shirozu, Fumitaka ;
Maruoka, Keiji .
SYNTHESIS-STUTTGART, 2009, (09) :1557-1563