Thieme Chemistry Journal Awardees - Where are They Now? Dibutyltin Dimethoxide Catalyzed N-Nitrosoaldol Reaction of Alkenyl Trichloroacetate

被引:9
作者
Yanagisawa, Akira [1 ]
Izumi, Youhei [2 ]
Takeshita, Satoshi [1 ]
机构
[1] Chiba Univ, Grad Sch Sci, Dept Chem, Inage Ku, Chiba 2638522, Japan
[2] Chiba Univ, Grad Sch Sci & Technol, Inage Ku, Chiba 2638522, Japan
关键词
tin catalyst; nitrosoaldol reaction; alpha-hydroxyamino ketone; alkenyl trichloroacetate; nitrosobenzene; ENANTIOSELECTIVE ALPHA-AMINOXYLATION; DIELS-ALDER REACTION; CARBONYL-COMPOUNDS; ORGANOCATALYTIC ROUTE; ENANTIOMERIC EXCESS; ALDOL SYNTHESIS; ALDOL/MICHAEL REACTION; ASYMMETRIC-SYNTHESIS; BRANCHED ALDEHYDES; AMINO-ALCOHOLS;
D O I
10.1055/s-0028-1087815
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nitrosoaldol reaction between alkenyl trichloroacetates and nitrosobenzene has been achieved using dibutyltin dimethoxide as a catalyst, which is regenerated in the presence of methanol. The corresponding alpha-hydroxyamino ketones (N-adducts) have exclusively formed not only from cyclic alkenyl trichloroacetates but also from acyclic ones.
引用
收藏
页码:716 / 719
页数:4
相关论文
共 53 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]   Origins of selectivities in proline-catalyzed α-aminoxylations [J].
Cheong, PHY ;
Houk, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (43) :13912-13913
[4]   The direct catalytic asymmetric α-aminooxylation reaction:: Development of stereoselective routes to 1,2-diols and 1,2-amino alcohols and density functional calculations [J].
Córdova, A ;
Sundén, H ;
Bogevig, A ;
Johansson, M ;
Himo, F .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (15) :3673-3684
[5]   Sugar-assisted kinetic resolution of amino acids and amplification of enantiomeric excess of organic molecules [J].
Cordova, Armando ;
Sunden, Henrik ;
Xu, Yongmei ;
Ibrahem, Ismail ;
Zou, Weibiao ;
Engqvist, Magnus .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (21) :5446-5451
[6]   Highly enantioselective α-aminoxylation of aldehydes and ketones with a polymer-supported organocatalyst [J].
Font, Daniel ;
Bastero, Amaia ;
Sayalero, Sonia ;
Jimeno, Ciril ;
Pericas, Miquel A. .
ORGANIC LETTERS, 2007, 9 (10) :1943-1946
[7]   An efficient organocatalytic route to the atorvastatin side-chain [J].
George, Shyla ;
Sudalai, Arumugam .
TETRAHEDRON LETTERS, 2007, 48 (48) :8544-8546
[8]   L-prolinamide-catalyzed direct nitroso aldol reactions of α-branched aldehydes:: a distinct regioselectivity from that with L-proline [J].
Guo, HM ;
Cheng, L ;
Cun, LF ;
Gong, LZ ;
Mi, AQ ;
Jiang, YZ .
CHEMICAL COMMUNICATIONS, 2006, (04) :429-431
[9]   A highly active 4-siloxyproline catalyst for asymmetric synthesis [J].
Hayashi, Y ;
Yamaguchi, J ;
Hibino, K ;
Sumiya, T ;
Urushima, T ;
Shoji, M ;
Hashizume, D ;
Koshino, H .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (12) :1435-1439
[10]   Direct proline-catalyzed asymmetric α-aminoxylation of aldehydes and ketones [J].
Hayashi, Y ;
Yamaguchi, J ;
Sumiya, T ;
Hibino, K ;
Shoji, M .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (18) :5966-5973