Enantioselective synthesis of highly functionalised amides by copper-catalysed vinylogous Mukaiyama aldol reaction

被引:47
|
作者
Frings, Marcus [1 ]
Goedert, Daniel [1 ]
Bolm, Carsten [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
关键词
LEWIS-BASE ACTIVATION; C-1-SYMMETRIC AMINOSULFOXIMINES; REVISED STRUCTURES; ADDITION-REACTIONS; NATURAL-PRODUCTS; MANNICH REACTION; PALMEROLIDE-A; LIGANDS; SULFOXIMINES; ALDEHYDES;
D O I
10.1039/c0cc00996b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Amides with quaternary stereogenic centers have been synthesised by catalytic asymmetric vinylogous Mukaiyama aldol reactions. The chiral copper-sulfoximine catalyst gives rise to products with moderate to good yields and up to 92% ee.
引用
收藏
页码:5497 / 5499
页数:3
相关论文
共 50 条
  • [1] Hydrogen bond catalyzed enantioselective vinylogous Mukaiyama aldol reaction
    Gondi, VB
    Gravel, M
    Rawal, VH
    ORGANIC LETTERS, 2005, 7 (25) : 5657 - 5660
  • [2] Total synthesis of khafrefungin using highly stereoselective vinylogous mukaiyama aldol reaction
    Shirokawa, Shin-ichi
    Shinoyama, Mariko
    Ooi, Isao
    Hosokawa, Seijiro
    Nakazaki, Atsuo
    Kobayashi, Susumu
    ORGANIC LETTERS, 2007, 9 (05) : 849 - 852
  • [3] Enantioselective vinylogous Mukaiyama aldol reaction of α-ketoesters under bifunctional organocatalysis
    del Rio-Rodriguez, Roberto
    Laina-Martin, Victor
    Fernandez-Salas, Jose A.
    Aleman, Jose
    CHEMICAL COMMUNICATIONS, 2021, 57 (88) : 11665 - 11668
  • [4] Diastereodivergent Vinylogous Mukaiyama Aldol Reaction
    Landsberg, Dirk
    Hartmann, Olaf
    Eggert, Ulrike
    Kalesse, Markus
    SYNLETT, 2013, 24 (09) : 1105 - 1108
  • [5] First total synthesis of salinipyrone A using highly stereoselective vinylogous Mukaiyama aldol reaction
    Ramesh, Palakuri
    Meshram, Harshadas Mitaram
    TETRAHEDRON, 2012, 68 (45) : 9289 - 9292
  • [6] Organocatalyzed Highly Enantioselective and anti-Selective Construction of γ-Butenolides through Vinylogous Mukaiyama Aldol Reaction
    Zhu, Ning
    Ma, Bao-Chun
    Zhang, Yong
    Wang, Wei
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (08) : 1291 - 1295
  • [7] Enantioselective synthesis of polyketide segments through vinylogous Mukaiyama aldol reactions
    Simsek, Serkan
    Kalesse, Markus
    TETRAHEDRON LETTERS, 2009, 50 (26) : 3485 - 3488
  • [8] Enantioselective vinylogous aldol reaction between β,γ-unsaturated amides and isatins
    Hu, Jun-Yi
    Fu, Jun-Hao
    Li, Tian-Ze
    Sha, Feng
    Wu, Xin-Yan
    NEW JOURNAL OF CHEMISTRY, 2024, 48 (29) : 13126 - 13130
  • [9] The vinylogous Mukaiyama aldol reaction (VMAR) in natural product synthesis
    Kalesse, Markus
    Cordes, Martin
    Symkenberg, Gerrit
    Lu, Hai-Hua
    NATURAL PRODUCT REPORTS, 2014, 31 (04) : 563 - 594
  • [10] Chiral amides via copper-catalysed enantioselective conjugate addition
    Schoonen, Anne K.
    Angeles Fernandez-Ibanez, M.
    Fananas-Mastral, Martin
    Teichert, Johannes F.
    Feringa, Ben L.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (01) : 36 - 41