Highly Diastereo- and Enantioselective Organocatalytic Michael Addition of α-Ketoamides to Nitroalkenes

被引:93
作者
Basle, Olivier [1 ]
Raimondi, Wilfried [1 ]
Sanchez Duque, Maria del Mar [1 ]
Bonne, Damien [1 ]
Constantieux, Thierry [1 ]
Rodriguez, Jean [1 ]
机构
[1] Aix Marseille Univ, CNRS, Ctr St Jerome, iSm2,UMR 6263,Serv 531, F-13397 Marseille, France
关键词
ASYMMETRIC CONJUGATE ADDITION; MANNICH-TYPE REACTIONS; DIRECT ALDOL REACTION; STEREOSELECTIVE-SYNTHESIS; 1,3-DICARBONYL COMPOUNDS; POLYKETIDE SYNTHASES; NITROALDOL REACTION; BOND FORMATION; KETO ESTERS; NITROOLEFINS;
D O I
10.1021/ol102289g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first organocatalytic enantio- and diastereoselective conjugate addition of alpha-ketoamides to nitroalkenes has been achieved using a bifunctional amino thiourea catalyst. In this new approach, the substrate amide proton plays a critical role in the formation of the Michael anti-adducts in high yields and high stereoselectivities. To illustrate the high synthetic potential of this methodology, the diastereo- and enantioselective synthesis of a hexasubstituted cyclohexane via a Michael-Michael-Henry cascade reaction is described.
引用
收藏
页码:5246 / 5249
页数:4
相关论文
共 67 条
  • [1] Organocatalytic Domino Reactions
    Alba, Andrea-Nekane
    Companyo, Xavier
    Viciano, Monica
    Rios, Ramon
    [J]. CURRENT ORGANIC CHEMISTRY, 2009, 13 (14) : 1432 - 1474
  • [2] Asymmetric 1,4-Addition of Oxazolones to Nitroalkenes by Bifunctional Cinchona Alkaloid Thiourea Organocatalysts: Synthesis of α,α-Disubstituted α-Amino Acids
    Aleman, Jose
    Milelli, Andrea
    Cabrera, Silvia
    Reyes, Efraim
    Jorgensen, Karl Anker
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (35) : 10958 - 10966
  • [3] Use of β,γ-Unsaturated α-Ketocarbonyls for a Totally Regioselective Oxidative Multicomponent Synthesis of Polyfunctionalized Pyridines
    Allais, Christophe
    Constantieux, Thierry
    Rodriguez, Jean
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (47) : 12945 - 12948
  • [4] Highly Efficient Synthesis of trans-β,γ-Unsaturated α-Keto Amides
    Allais, Christophe
    Constantieux, Thierry
    Rodriguez, Jean
    [J]. SYNTHESIS-STUTTGART, 2009, (15): : 2523 - 2530
  • [5] Organocatalytic asymmetric conjugate additions
    Almasi, Diana
    Alonso, Diego A.
    Najera, Carmen
    [J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (03) : 299 - 365
  • [6] Towards organocatalytic polyketide synthases with diverse electrophile scope: Trifluoroethyl thioesters as nucleophiles in organocatalytic Michael reactions and beyond
    Alonso, Diego A.
    Kitagaki, Shinji
    Utsumi, Naoto
    Barbas, Carlos F., III
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (24) : 4588 - 4591
  • [7] Highly Regio- and Diastereoselective Oxazol-5-one Addition to Nitrostyrenes
    Balaguer, Andrea-Nekane
    Companyo, Xavier
    Calvet, Teresa
    Font-Bardia, Merce
    Moyano, Albert
    Rios, Ramon
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (02) : 199 - 203
  • [8] Synthesis of Binaphthyl Sulfonimides and Their Application in the Enantioselective Michael Addition of Ketones to Nitroalkenes
    Ban, Shurong
    Du, Da-Ming
    Liu, Han
    Yang, Wen
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (27) : 5160 - 5164
  • [9] An Organocatalytic Asymmetric Nazarov Cyclization
    Basak, Ashok K.
    Shimada, Naoyuki
    Bow, William F.
    Vicic, David A.
    Tius, Marcus A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (24) : 8266 - +
  • [10] Organocatalysis-after the gold rush
    Bertelsen, Soren
    Jorgensen, Karl Anker
    [J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) : 2178 - 2189