Straightforward and Stereoselective Synthesis of α,β-Diamino Acid Derivatives by Means of an Organocatalyzed Decarboxylative Mannich Reaction

被引:12
作者
Singjunla, Yuttapong [1 ]
Baudoux, Jerome [1 ]
Rouden, Jacques [1 ]
机构
[1] Normandie Univ, LCMT, ENSICAEN, UNICAEN,CNRS, 6 Blvd Marechal Juin, F-14000 Caen, France
关键词
Diastereoselectivity; Organocatalysis; Decarboxylation; Mannich reaction; Synthetic methods; RESISTANT ENTEROCOCCI VRE; BETA-AMINO ESTERS; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; GLYCOPEPTIDE ANTIBIOTICS; BIOLOGICAL SIGNIFICANCE; DESIGN; ANTRIMYCIN; ACCESS; (2S; 3R)-CAPREOMYCIDINE;
D O I
10.1002/ejoc.201700468
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A rapid and convenient method has been developed for the stereoselective synthesis of alpha,beta-diamino acid derivatives from amido-substituted malonic acid half oxyesters (MAHOs) and imines. The anti products were obtained with a diastereomeric ratio up to 99: 1 by using a decarboxylative Mannich reaction catalyzed by commercially available 1,4-diazabicyclo[2.2.2] octane (DABCO).
引用
收藏
页码:3240 / 3243
页数:4
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共 45 条
  • [1] Recent advances in the synthesis of new glycopeptide antibiotics
    Ashford, Polly-Anna
    Bew, Sean P.
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (03) : 957 - 978
  • [2] Environmentally benign metal-free decarboxylative aldol and Mannich reactions
    Baudoux, Jerome
    Lefebvre, Pierre
    Legay, Remi
    Lasne, Marie-Claire
    Rouden, Jacques
    [J]. GREEN CHEMISTRY, 2010, 12 (02) : 252 - 259
  • [3] An Efficient Combinatorial Synthesis of Allocolchicine Analogues via a Triple Cascade Reaction and their Evaluation as Inhibitors of Insulin Aggregation
    Bhowmik, Subhendu
    Khanna, Shruti
    Srivastava, Kumkum
    Hasanain, Mohammad
    Sarkar, Jayanta
    Verma, Sandeep
    Batra, Sanjay
    [J]. CHEMMEDCHEM, 2013, 8 (11) : 1767 - 1772
  • [4] Glycopeptide antibiotics: Back to the future
    Butler, Mark S.
    Hansford, Karl A.
    Blaskovich, Mark At
    Halai, Reena
    Cooper, Matthew A.
    [J]. JOURNAL OF ANTIBIOTICS, 2014, 67 (09) : 631 - 644
  • [5] NAPSAMYCINS, NEW PSEUDOMONAS ACTIVE ANTIBIOTICS OF THE MUREIDOMYCIN FAMILY FROM STREPTOMYCES SP HIL Y-82,11372
    CHATTERJEE, S
    NADKARNI, SR
    VIJAYAKUMAR, EKS
    PATEL, MV
    GANGULI, BN
    FEHLHABER, HW
    VERTESY, L
    [J]. JOURNAL OF ANTIBIOTICS, 1994, 47 (05) : 595 - 598
  • [6] Synthesis of novel 7-oxo and 7-hydroxy trifluoroallocolchicinoids with cytotoxic effect
    Chosson, Elizabeth
    Santoro, Francesca
    Rochais, Christophe
    Santos, Jana Sopkova-de Oliveira
    Legay, Remi
    Thoret, Sylviane
    Cresteil, Thierry
    Sinicropi, Maria Stefania
    Besson, Thierry
    Dallemagne, Patrick
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (08) : 2614 - 2623
  • [7] Direct catalytic enantioselective mannich reactions:: Synthesis of protected anti-α,β-diamino acids
    Cutting, Gary A.
    Stainforth, Nikki E.
    John, Matthew P.
    Kociok-Koehn, Gabriele
    Willis, Michael C.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (35) : 10632 - +
  • [8] Asymmetric synthesis of syn-(2R,3S)- and anti-(2S,3 s)-ethyl diamino-3-phenylpropanoates from N-(benzylidene)-p-toluenesulfinamide and glycine enolates
    Davis, FA
    Deng, JH
    [J]. ORGANIC LETTERS, 2004, 6 (16) : 2789 - 2792
  • [9] Asymmetric synthesis of anti- and syn-2,3-diamino esters using sulfinimines.: Water and concentration effects
    Davis, Franklin A.
    Zhang, Yanfeng
    Qiu, Hui
    [J]. ORGANIC LETTERS, 2007, 9 (05) : 833 - 836
  • [10] Asymmetric synthesis of (2S,3R)-capreomycidine and the total synthesis of capreomycin IB
    DeMong, DE
    Williams, RM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (28) : 8561 - 8565