Recent developments in functionalization of acyclic α-keto amides

被引:31
作者
Muthukumar, Alagesan [1 ]
Sangeetha, Subramani [1 ]
Sekar, Govindasamy [1 ]
机构
[1] Indian Inst Technol Madras, Dept Chem, Madras 600036, Tamil Nadu, India
关键词
PICTET-SPENGLER REACTIONS; SUZUKI-MIYAURA REACTION; MANNICH-TYPE REACTIONS; ONE-POT SYNTHESIS; METAL-FREE; CHEMOSELECTIVE REDUCTION; ASYMMETRIC-SYNTHESIS; CHLOROPEPTIN-I; INTERMOLECULAR HYDROACYLATION; INTRAMOLECULAR CYCLIZATION;
D O I
10.1039/c8ob01423j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
alpha-Keto amides are a key frame in biology, medicinal chemistry and synthetic chemistry as drug molecules and key intermediates. Based on the structural aspect, an acyclic alpha-keto amide has multiple reactive centres which have electrophilic and nucleophilic characters. In this review, we focus on the recent developments of both asymmetric and achiral reactions involving acyclic alpha-keto amides as the reactants for the synthesis of cyclic and acyclic molecules through the formation of C-C, C-O, C-N and C-H bonds. Based on the reactivity of alpha-keto amides, this article is divided into three major classes: 1. mono-functionalization, 2. dual functionalization, and 3. triple functionalization of alpha-keto amides, which are further divided into sub-classes as well. Over 50 examples including our own work have been demonstrated for the functionalization of acyclic alpha-keto amides since 1992. Moreover, the usefulness of alpha-keto amides is shown for the synthesis of biologically active molecules, synthetic intermediates, heterocycles, valuable compounds, building blocks and metal complexes.
引用
收藏
页码:7068 / 7083
页数:17
相关论文
共 117 条
  • [1] Exploiting the Reactivity of 1,2-Ketoamides: Enantioselective Synthesis of Functionalized Pyrrolidines and Pyrrolo-1,4-benzodiazepine-2,5-diones
    Acosta, Paola
    Becerra, Diana
    Goudedranche, Sebastien
    Quiroga, Jairo
    Constantieux, Thierry
    Bonne, Damien
    Rodriguez, Jean
    [J]. SYNLETT, 2015, 26 (11) : 1591 - 1595
  • [2] 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
  • [3] Highly Efficient Synthesis of trans-β,γ-Unsaturated α-Keto Amides
    Allais, Christophe
    Constantieux, Thierry
    Rodriguez, Jean
    [J]. SYNTHESIS-STUTTGART, 2009, (15): : 2523 - 2530
  • [4] POSTSTATIN, A NEW INHIBITOR OF PROLYL ENDOPEPTIDASE, PRODUCED BY STREPTOMYCES-VIRIDOCHROMOGENES MH534-30F3 .1. TAXONOMY, PRODUCTION, ISOLATION, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL-ACTIVITIES
    AOYAGI, T
    NAGAI, M
    OGAWA, K
    KOJIMA, F
    OKADA, M
    IKEDA, T
    HAMADA, M
    TAKEUCHI, T
    [J]. JOURNAL OF ANTIBIOTICS, 1991, 44 (09) : 949 - 955
  • [5] Asao N, 2001, ANGEW CHEM INT EDIT, V40, P3206, DOI 10.1002/1521-3773(20010903)40:17<3206::AID-ANIE3206>3.0.CO
  • [6] 2-5
  • [7] Influence of steric and electronic perturbations on the polymerization activities of α-iminocarboxamide nickel complexes
    Azoulay, Jason D.
    Itigaki, Koji
    Wu, Guang
    Bazan, Guillermo C.
    [J]. ORGANOMETALLICS, 2008, 27 (10) : 2273 - 2280
  • [8] TORSIONAL BARRIERS IN ALPHA-KETO AMIDES - MODEL STUDIES RELATED TO THE BINDING-SITE OF FK506
    BACH, RD
    MINTCHEVA, I
    KRONENBERG, WJ
    SCHLEGEL, HB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) : 6135 - 6138
  • [9] Highly Diastereo- and Enantioselective Organocatalytic Michael Addition of α-Ketoamides to Nitroalkenes
    Basle, Olivier
    Raimondi, Wilfried
    Sanchez Duque, Maria del Mar
    Bonne, Damien
    Constantieux, Thierry
    Rodriguez, Jean
    [J]. ORGANIC LETTERS, 2010, 12 (22) : 5246 - 5249
  • [10] Synthesis of new chiral hydroxy oxazolines and their use in the catalytic asymmetric phenyl transfer to aldehydes
    Bolm, C
    Schmidt, F
    Zani, L
    [J]. TETRAHEDRON-ASYMMETRY, 2005, 16 (07) : 1367 - 1376