Zinc tetrafluoroborate catalyzed Mannich-type reaction of aldimines and silyl enol ethers in aqueous medium

被引:71
|
作者
Ranu, BC [1 ]
Samanta, S [1 ]
Guchhait, SK [1 ]
机构
[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, W Bengal, India
关键词
Mannich reaction; beta-amino carbonyl compounds; zinc tetrafluoroborate;
D O I
10.1016/S0040-4020(01)01177-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The use of zinc tetrafluoroborate as a catalyst in Mannich-type addition of silyl enol ethers to aldimines in aqueous THF provides beta-amino ketones or beta-amino esters in high yields. A one-pot reaction of an aldehyde, amine and silyl enolate also works well. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:983 / 988
页数:6
相关论文
共 50 条
  • [1] Lewis base catalyzed Mannich-type reactions between trimethylsilyl enol ethers and aldimines
    Fujisawa, Hidehiko
    Takahashi, Eiki
    Mukaiyama, Teruaki
    CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (19) : 5082 - 5093
  • [2] Chiral Bronsted Acid-Catalyzed Stereoselective Mannich-Type Reaction of Azlactones with Aldimines
    Avila, Eloah P.
    Justo, Rodrigo M. S.
    Goncalves, Vanessa P.
    Pereira, Adriane A.
    Diniz, Renata
    Amarante, Giovanni W.
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01): : 590 - 594
  • [3] STUDIES OF THE ZINC(II) CATALYZED ADDITION OF SILYL ENOL ETHERS TO CYCLIC ENOL ETHERS
    STUDLEY, JR
    WILLS, M
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 455 (1-2) : C3 - C5
  • [4] HBF4 catalyzed Mannich-type reaction in aqueous media
    Akiyama, T
    Takaya, J
    Kagoshima, H
    SYNLETT, 1999, (07) : 1045 - 1048
  • [5] Calcium catalyzed Mukaiyama-Mannich addition of silyl enol ethers to nitrones
    Congdon, Elizabeth A.
    Nolin, Kristine A.
    CATALYSIS COMMUNICATIONS, 2016, 79 : 35 - 38
  • [6] Novel one-pot mannich-type reaction in water:: Indium trichloride-catalyzed condensation of aldehydes, amines and silyl enol ethers for the synthesis of β-amino ketones and esters
    Loh, TP
    Wei, LL
    TETRAHEDRON LETTERS, 1998, 39 (3-4) : 323 - 326
  • [7] Stereoselective ZrCl4-Catalyzed Mannich-type Reaction of β-Keto Esters with Chiral Trifluoromethyl Aldimines
    Parise, Luca
    Pellacani, Lucio
    Sciubba, Fabio
    Trulli, Laura
    Fioravanti, Stefania
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (16): : 8300 - 8306
  • [8] Group 4 metal triflates as efficient catalysts for allylations of imines with allyltributylstannane and Mannich-type reactions of imines with silyl enol ethers
    Kobayashi, S
    Iwamoto, S
    Nagayama, S
    SYNLETT, 1997, (09) : 1099 - 1101
  • [9] Mannich-type allylic C-H functionalization of enol silyl ethers under photoredox-thiol hybrid catalysis
    Nakashima, Tsubasa
    Ohmatsu, Kohsuke
    Ooi, Takashi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (01) : 141 - 145
  • [10] Practical Synthesis of Natural Amino Acid Derivatives: Hf(OTf)4-Catalyzed Mannich-Type Reaction of Ketene Silyl Acetals or Enol Silyl Ethers with N,O-Acetals as a Glycine Cation Equivalent
    Sakai, Norio
    Sato, Asuka
    Konakahara, Takeo
    SYNLETT, 2009, (09) : 1449 - 1452