Spontaneous and diastereoselective aldol reactions of cyclic β-amino ketones in the presence of water

被引：15
|
作者：
Lazny, Ryszard [1 ]
Nodzewska, Aneta [1 ]
Tomczuk, Iwona [1 ]
机构：
[1] Univ Bialystok, Inst Chem, PL-15399 Bialystok, Poland
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 43期
关键词：
Aldol reaction; Reaction in water; Tropinone; Granatanone; CATALYSIS; DEPROTONATION; PURE;
D O I：
10.1016/j.tetlet.2011.08.107
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Direct aldol reactions of 4-methyl-1-piperidone, tropinone and granatanone (pseudopelletierine) take place spontaneously in the presence of water without any catalyst or additional reagents. The anti/syn-diastereoselectivity of the aqueous aldol reaction depends on the amount of water used. The syn-selectivity of the reaction is probably due to the thermodynamic control. Excellent atom economy and low E factors together with anti-selectivity as high as 98:2 for the tropinone aldol were obtained. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5680 / 5683
页数：4
相关论文
共 50 条
  • [1] HIGHLY DIASTEREOSELECTIVE ALDOL REACTIONS OF ALPHA-AMINO METHYL KETONES
    LAGU, BR
    CRANE, HM
    LIOTTA, DC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 206 : 428 - ORGN
  • [2] HIGHLY DIASTEREOSELECTIVE ALDOL REACTIONS OF CHIRAL METHYL KETONES
    LAGU, BR
    CRANE, HM
    LIOTTA, DC
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16): : 4191 - 4193
  • [3] A DFT study of the origins of the stereoselectivity in the aldol reaction of bicyclic amino ketones in the presence of water
    Lazny, Ryszard
    Ratkiewicz, Artur
    Nodzewska, Aneta
    Wysocka, Joanna
    TETRAHEDRON LETTERS, 2012, 53 (44) : 5871 - 5874
  • [4] Iron(III) chloride as a water-compatible Lewis acid for diastereoselective aldol reactions in water in the presence of a surfactant
    Aoyama, N
    Manabe, K
    Kobayashi, S
    CHEMISTRY LETTERS, 2004, 33 (03) : 312 - 313
  • [5] Boron aldol reactions of amino acid derived ketones.
    Paterson, I
    Mackay, AC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U106 - U106
  • [6] Diastereoselective aldol reactions of enolates generated from vicinally substituted trimethylsilylmethyl cyclopropyl ketones
    Yadav, VK
    Balamurugan, R
    ORGANIC LETTERS, 2003, 5 (23) : 4281 - 4284
  • [7] Transition metal-catalyzed diastereoselective aldol reactions of prochiral ketones with methyl isocyanoacetate
    Soloshonok, VA
    Kacharov, AD
    Avilov, DV
    Hayashi, T
    TETRAHEDRON LETTERS, 1996, 37 (43) : 7845 - 7848
  • [8] Enantioselective aldol reaction of cyclic ketones with aryl aldehydes catalyzed by a cyclohexanediamine derived salt in the presence of water
    Lin, Jin-Hong
    Zhang, Cheng-Pan
    Xiao, Ji-Chang
    GREEN CHEMISTRY, 2009, 11 (11) : 1750 - 1753
  • [9] Diastereoselective intermolecular cobalt-catalyzed reductive aldol reactions of α,β-unsaturated Amides with ketones
    Lumby, Ralph J. R.
    Joensuu, Pekka M.
    Lam, Hon Wai
    ORGANIC LETTERS, 2007, 9 (21) : 4367 - 4370
  • [10] Enantioselective radical reactions: Stereoselective aldol synthesis from cyclic ketones
    Sibi, Mukund P.
    Nad, Sukanya
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (48) : 9231 - 9234
12345