Alternative strategies for the stereoselective synthesis of enantioenriched 6-arylated piperidin-2-ones

被引:11
|
作者
Sallio, Romain [1 ,2 ]
Lebrun, Stephane [1 ,2 ]
Agbossou-Niedercorn, Francine [1 ,3 ,4 ]
Michon, Christophe [1 ,3 ,4 ]
Deniau, Eric [1 ,2 ]
机构
[1] Univ Lille Nord France, F-59000 Lille, France
[2] Univ Lille 1, EA CMF 4478, Chim Organ Phys Lab, F-59655 Villeneuve Dascq, France
[3] UCCS, CNRS, UMR 8181, F-59655 Villeneuve Dascq, France
[4] ENSCL, CCM CCCF, F-59652 Villeneuve Dascq, France
关键词
HIGHLY ENANTIOSELECTIVE HYDROGENATION; ASYMMETRIC-SYNTHESIS; CATALYZED HYDROGENATION; SUZUKI-MIYAURA; PHOSPHATES; ALKALOIDS; CYCLOADDITION; COMPLEX; BOND; N; N-DIALKYLHYDRAZONES;
D O I
10.1016/j.tetasy.2012.06.024
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Two alternative synthetic approaches to a variety of enantioenriched 6-arylated piperidin-2-ones have been developed. The first one is based on the hydrogenation of suitably arylated chiral cyclic enehydrazides. The second approach relies on the asymmetric catalytic hydrogenation of the corresponding N-alkylated precursors. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:998 / 1004
页数:7
相关论文
共 50 条
  • [31] Microwave-Assisted Multicomponent Synthesis of New 6-Arylated 5-Hydroxy-benzo[a]phenazine Derivatives and Their Potential Anti-inflammatory Activity
    Nguyen, Ha Thanh
    Thi, Thu Ha Nguyen
    Braire, Julien
    Thi, Tuyet Anh Dang
    Van, Tuyen Nguyen
    CHEMISTRYSELECT, 2023, 8 (01):
  • [32] Stereoselective synthesis of highly enantioenriched 3-methyl-2-cyclohexen-1-ones possessing an asymmetric quaternary carbon as C-4 or C-6: a sugar template approach
    Kubo, Hiroto
    Kozawa, Ikuko
    Takao, Ken-ichi
    Tadano, Kin-ichi
    TETRAHEDRON LETTERS, 2008, 49 (07) : 1203 - 1207
  • [33] Synthesis of N-arylated pyrrolidin-2-ones and morpholin-3-ones as potassium channel openers.
    Liang, PH
    Cheng, CY
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U116 - U116
  • [34] Synthesis, spectral characterization and DFT analysis for the validation of 2, 6 diaryl -piperidin-4-ones as potential sunscreens and UV filters
    Suresh, T.
    Sarveswari, S.
    Murugan, N. Arul
    Vijayakumar, V.
    Iniyavan, P.
    Srikanth, A.
    Jasinski, Jerry P.
    JOURNAL OF MOLECULAR STRUCTURE, 2015, 1099 : 560 - 566
  • [35] Synthesis and stereoselective oxidation of α-thio-β-chloropropenyloxazolidin-2-ones
    Kissane, Marie
    Murphy, Maureen
    Lawrence, Simon E.
    Maguire, Anita R.
    TETRAHEDRON-ASYMMETRY, 2010, 21 (20) : 2550 - 2558
  • [36] STEREOSELECTIVE SYNTHESIS OF HETEROCYCLES BY DESULFURIZATION OF CONDENSED THIAZOLIDIN-2-ONES
    HAMERSMA, JAM
    SPECKAMP, WN
    TETRAHEDRON, 1985, 41 (14) : 2861 - 2866
  • [37] Asymmetric synthesis of spiro 2-pyrrolidin-5-ones, 2-piperidin-6-ones and 1-isoindolin-3-ones.: Part 2:: N-acyliminium ion cyclisations with an internal alkene nucleophile
    Bahajaj, AA
    Vernon, JM
    Wilson, GD
    TETRAHEDRON, 2004, 60 (05) : 1247 - 1253
  • [38] STEREOSELECTIVE SYNTHESIS OF 5-ALPHA,7-BETA-DICYANOCHOLESTAN-6-ONES
    HABIB, R
    HUSAIN, M
    FAZAL, A
    HUSAIN, M
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1988, 27 (06): : 584 - 586
  • [39] Stereoselective One-Pot Synthesis of Dihydropyrimido[2,1-a]isoindole-6(2H)-ones
    Kramer, Philipp
    Schoenfeld, Julia
    Bolte, Michael
    Manolikakes, Georg
    ORGANIC LETTERS, 2018, 20 (01) : 178 - 181
  • [40] Synthesis of 2-hydroxymethylpyrimidin-6-ones
    Shvachkin, YP
    Smirnova, AP
    Ermak, NM
    Knyazeva, VV
    Maiorova, VF
    ZHURNAL OBSHCHEI KHIMII, 1999, 69 (01): : 166 - 166