A rapid catalytic asymmetric synthesis of 1,3,4-trisubstituted pyrrolidines

被引：25
|
作者：
Belyk, KM
Beguin, CD
Palucki, M
Grinberg, N
DaSilva, J
Askin, D
Yasuda, N
机构：
[1] Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA
[2] Merck Res Labs, Dept Analyt Chem, Rahway, NJ 07065 USA
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 16期
关键词：
pyrrolidine; 1,3-dipolar cycloaddition; asymmetric 1,4-addition; rhodium-catalyzed; arylboronic acid;
D O I：
10.1016/j.tetlet.2004.02.114
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The asymmetric synthesis of 1,3,4-trisubstituted pyrrolidines was accomplished in two steps from readily available starting materials. A 1,3-dipolar cycloaddition of an azomethine ylide to a propiolate ester followed by a Rh-catalyzed asymmetric 1,4-arylation of the resulting pyrroline with an arylboronic acid provided the desired 1,3,4-trisubstituted pyrrolidine products in good to excellent enantioselectivities. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3265 / 3268
页数：4
相关论文
共 50 条
  • [1] Asymmetric synthesis of 1,3,4-trisubstituted pyrrolidines.
    Belyk, K
    Beguin, C
    Palucki, M
    Patel, M
    Dasilva, J
    Askin, D
    Yasuda, N
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U32 - U32
  • [2] Synthesis of a proposed 1,3,4-trisubstituted isoquinoline
    Yang, Hanbiao
    Sjogren, Eric
    TETRAHEDRON LETTERS, 2010, 51 (27) : 3524 - 3527
  • [3] A facile synthesis of 1,3,4-trisubstituted isoquinolines
    Yang, Hanbiao
    TETRAHEDRON LETTERS, 2009, 50 (25) : 3081 - 3083
  • [4] Synthesis of 1,3,4-trisubstituted pyrrolidines as meropenem adjuvants targeting New Delhi metallo-β-lactamase
    Jin, Wen Bin
    Xu, Chen
    Qi, Xiao Lin
    Zeng, Ping
    Gao, Wei
    Lai, Ki Hon
    Chiou, Jiachi
    Chan, Edward W. C.
    Leung, Yun-Chung
    Chan, Tak Hang
    Wong, Kwok-Yin
    Chen, Sheng
    Chan, Kin-Fai
    NEW JOURNAL OF CHEMISTRY, 2021, 45 (07) : 3515 - 3534
  • [5] A rapid assembly of homochiral 2,3,4-trisubstituted pyrrolidines
    Jones, RCF
    Howard, KJ
    Snaith, JS
    TETRAHEDRON LETTERS, 1997, 38 (09) : 1647 - 1650
  • [6] Synthesis of Cytotoxic 1,3,4-trisubstituted 2-azetidinones
    G. Veinberg
    R. Bokaldere
    K. Dikovskaya
    M. Vorona
    I. Kanepe
    I. Shestakova
    E. Yashchenko
    E. Lukevics
    Chemistry of Heterocyclic Compounds, 2003, 39 (5) : 587 - 593
  • [7] The synthesis of cytotoxic 1,3,4-trisubstituted azetidinones-2
    Veiberg, G
    Bokaldere, R
    Vorona, M
    Kanepe, I
    Shestakova, I
    Lukevics, E
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2003, (05): : 680 - 687
  • [8] PHOSPHODIESTERASE TYPE-IV (PDE-IV) INHIBITION - SYNTHESIS AND EVALUATION OF A SERIES OF 1,3,4-TRISUBSTITUTED PYRROLIDINES
    STAFFORD, JA
    VALVANO, NL
    FELDMAN, PL
    BRAWLEY, ES
    COWAN, DJ
    DOMANICO, PL
    LEESNITZER, MA
    ROSE, DA
    STIMPSON, SA
    STRICKLAND, AB
    UNWALLA, RJ
    VERGHESE, MW
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (17) : 1977 - 1982
  • [9] Efficient solid-phase synthesis of 1,3,4-trisubstituted β-thiolactams
    Méndez, L
    Delpiccolo, CML
    Mata, EG
    SYNLETT, 2005, (10) : 1563 - 1566
  • [10] Asymmetric Synthesis of 2,3,4-Trisubstituted Piperidines
    Kriis, Kadri
    Melnik, Triin
    Lips, Kristiina
    Juhanson, Ilona
    Kaabel, Sandra
    Jarving, Ivar
    Kanger, Tonis
    SYNTHESIS-STUTTGART, 2017, 49 (03): : 604 - 614
12345