FeCl3.6H2O catalyzed diastereoselective synthesis of (L)-menthyl 4-oxo-2-arylpiperidine-3-carboxylates

被引:3
作者
Syamala, Lakshmi V. R. Babu [1 ]
Bhat, Ramakrishna G. [1 ]
机构
[1] Indian Inst Sci Educ & Res, Dept Chem, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India
关键词
Catalysis; Cyclization; Chiral auxiliary; aza-Michael addition; Lewis acid; DIELS-ALDER REACTIONS; ASYMMETRIC-SYNTHESIS; CONCISE SYNTHESIS; ACID; PIPERIDINES; ALKALOIDS; PYRROLIDINE; SCAFFOLDS; AUXILIARY; IMINES;
D O I
10.1016/j.tetlet.2017.11.026
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient diastereoselective synthesis of substituted piperidines is accomplished by using catalytic amount of FeCl3:6H(2)O via intramolecular aza-Michael addition of carbamate on alkylidene beta-keto (L)menthyl esters in a very short time. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4836 / 4840
页数:5
相关论文
共 47 条
  • [1] Electronically rich N-substituted tetrahydroisoquinoline 3-carboxylic acid esters: concise synthesis and conformational studies
    Al-Horani, Rami A.
    Desai, Umesh R.
    [J]. TETRAHEDRON, 2012, 68 (08) : 2027 - 2040
  • [2] ASYMMETRIC-SYNTHESIS OF PIPECOLIC ACID-DERIVATIVES USING THE AZA-DIELS-ALDER REACTION
    BAILEY, PD
    BROWN, GR
    KORBER, F
    REED, A
    WILSON, RD
    [J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (12) : 1263 - 1282
  • [3] ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF PIPECOLIC ACID-DERIVATIVES USING THE AZA-DIELS-ALDER REACTION OF IMINES WITH DIENES
    BAILEY, PD
    WILSON, RD
    BROWN, GR
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (05): : 1337 - 1340
  • [4] Bailey PD, 1998, CHEM COMMUN, V633
  • [5] An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles
    Baumann, Marcus
    Baxendale, Ian R.
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 2265 - 2319
  • [6] ASYMMETRIC-SYNTHESIS .32. A NEW ACCESS TO ENANTIOMERICALLY PURE (S)-(-)-PIPECOLIC ACID AND 2-ALKYLATED OR 6-ALKYLATED DERIVATIVES
    BERRIEN, JF
    ROYER, J
    HUSSON, HP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (14) : 3769 - 3774
  • [7] Braekman J.C., 1990, Studies in Natural Products Chemistry, V6, P421
  • [8] Synthesis of piperidines
    Buffat, MGP
    [J]. TETRAHEDRON, 2004, 60 (08) : 1701 - 1729
  • [9] Michael additions catalyzed by transition metals and lanthanide species.: A review
    Comelles, J
    Moreno-Mañas, M
    Vallribera, A
    [J]. ARKIVOC, 2005, : 207 - 238
  • [10] Synthesis of glycoproteins
    Davis, BG
    [J]. CHEMICAL REVIEWS, 2002, 102 (02) : 579 - 601