Iron(II)-Derived Lewis Acid/Surfactant Combined Catalysis for the Enantioselective Mukaiyama Aldol Reaction in Pure Water

被引：21
|
作者：
Lafantaisie, Mathieu [1 ]
Mirabaud, Anais [1 ]
Plancq, Baptiste [1 ]
Ollevier, Thierry [1 ]
机构：
[1] Univ Laval, Dept Chim, Quebec City, PQ G1V 0A6, Canada
来源：
CHEMCATCHEM | 2014年 / 6卷 / 08期
基金：
加拿大自然科学与工程研究理事会; 加拿大创新基金会;
关键词：
aldol reaction; enantioselectivity; iron; Lewis acids; surfactants; SURFACTANT-COMBINED CATALYST; SILYL ENOL ETHERS; AQUEOUS-MEDIA; ORGANIC-REACTIONS; ACID CATALYSTS; ASYMMETRIC CATALYSIS; LIGANDS; IRON; HYDROXYMETHYLATION; TRIFLATE;
D O I：
10.1002/cctc.201402029
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The catalytic asymmetric Mukaiyama aldol reaction in pure water was performed by using a combination of iron(II) dodecyl sulfate, a chiral bipyridine ligand, and benzoic acid. By using the obtained iron(II)-derived Lewis acid/surfactant combined catalyst, the desired products were afforded in good yields with high diastereo- and enantioselectivities.
引用
收藏
页码：2244 / 2247
页数：4
相关论文
共 50 条
  • [41] Hetero Diels-Alder vs Mukaiyama aldol pathways in the reaction of monoactivated dienes and aldehydes. A Lewis acid study
    Mujica, MT
    Afonso, MM
    Galindo, A
    Palenzuela, JA
    TETRAHEDRON, 1996, 52 (06) : 2167 - 2176
  • [42] Lewis acid-Lewis acid heterobimetallic cooperative catalysis: Mechanistic studies and application in enantioselective aza-Michael reaction
    Yamagiwa, N
    Qin, HB
    Matsunaga, S
    Shibasaki, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) : 13419 - 13427
  • [43] Hetero Diels-Alder vs Mukaiyama aldol pathways in the reaction of monoactivated dienes and aldehydes. A Lewis acid study
    Mujica, M. T.
    Afonso, M. M.
    Galindo, A.
    Palenzuela, J. A.
    Tetrahedron, 52 (06):
  • [44] Asymmetric Mukaiyama aldol reaction of silyl enol ethers with aldehydes using a polymer-supported chiral Lewis acid catalyst
    Itsuno, S
    Arima, S
    Haraguchi, N
    TETRAHEDRON, 2005, 61 (51) : 12074 - 12080
  • [45] Copper-Catalyzed Enantioselective Mukaiyama Aldol Reaction of Silyl Enol Ethers with Isatin-Derived Oxindolyl β,γ-Unsaturated α-Keto Esters
    Lu, Wenjing
    Li, Jindong
    Lu, Yangmian
    Zha, Zhenggen
    Wang, Zhiyong
    CHEMISTRYSELECT, 2021, 6 (03): : 410 - 414
  • [46] LEWIS-ACID CATALYSIS OF A DIELS-ALDER REACTION IN WATER
    OTTO, S
    ENGBERTS, JBFN
    TETRAHEDRON LETTERS, 1995, 36 (15) : 2645 - 2648
  • [47] Studies on the role of Lewis basicity of the aldehydes utilized in the enantioselective Mukaiyama aldol reaction promoted by chiral 1,3,2-oxazaborolidin-5-ones
    Simpura, I
    Nevalainen, V
    TETRAHEDRON-ASYMMETRY, 1999, 10 (01) : 7 - 9
  • [48] Enamine-Metal Lewis Acid Bifunctional Catalysis: Application to Direct Asymmetric Aldol Reaction of Ketones
    Xu, Zhenghu
    Daka, Philias
    Budik, Ilya
    Wang, Hong
    Bai, Fu-Quan
    Zhang, Hong-Xing
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (27) : 4581 - 4585
  • [49] Tetranuclear Hafnium(TV) and Zirconium(IV) Cationic Complexes Sandwiched between Two Di-Lacunary Species of α-Keggin Polyoxometalates: Lewis Acid Catalysis of the Mukaiyama-Aldol Reaction
    Nomiya, Kenji
    Ohta, Kazuaki
    Sakai, Yoshitaka
    Hosoya, Taka-aki
    Ohtake, Atsushi
    Takakura, Akira
    Matsunaga, Satoshi
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2013, 86 (07) : 800 - 812
  • [50] Unprecedented preference for aldehyde over acetal in organotin Lewis acid-promoted Mukaiyama-aldol reaction of ketene silyl acetals
    Otera, J
    Chen, JX
    SYNLETT, 1996, (04) : 321 - 323
12345