Amine-catalyzed direct aldol addition

被引：74
|
作者：
Markert, Morris [1 ]
Mulzer, Michael [1 ]
Schetter, Bernd [1 ]
Mahrwald, Rainer [1 ]
机构：
[1] Humboldt Univ, Inst Chem, D-12489 Berlin, Germany
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 23期
关键词：
D O I：
10.1021/ja071926a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient organo-catalytic, highly syn-stereoselective method for aldol additions between enolizable aldehydes and hydroxyacetone as well as dihydroxyacetone is disclosed. Reactions proceed in the presence of tertiary amines at room temperature. The aldol adducts can be obtained in good to high yields and with high degrees of syn-diastereoselectivity. This new aldol reaction provides an operationally simple protocol for the stereocontrolled synthesis of carbohydrates
引用
收藏
页码：7258 / +
页数：3
相关论文
共 50 条
  • [1] Stereoselective Direct Amine-Catalyzed Decarboxylative Aldol Addition
    Rohr, Kerstin
    Mahrwald, Rainer
    ORGANIC LETTERS, 2011, 13 (07) : 1878 - 1880
  • [2] ROLE OF ADDITIVES IN CHIRAL AMINE-CATALYZED DIRECT ALDOL REACTION
    Sutar, R. L.
    Joshi, N. N.
    SYNTHETIC COMMUNICATIONS, 2014, 44 (03) : 352 - 360
  • [3] Amine-catalyzed aldol condensation in the presence of lithium perchlorate
    Arnold, A
    Markert, M
    Mahrwald, R
    SYNTHESIS-STUTTGART, 2006, (07): : 1099 - 1102
  • [4] Amine-Catalyzed Direct Aldol Reactions of Hydroxy- and Dihydroxyacetone: Biomimetic Synthesis of Carbohydrates
    Popik, Oskar
    Pasternak-Soder, Monika
    Lesniak, Katarzyna
    Jawiczuk, Magdalena
    Gorecki, Marcin
    Frelek, Jadwiga
    Mlynarski, Jacek
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (12): : 5728 - 5739
  • [5] Amine-Catalyzed Decarboxylative Aldol Reaction of β-Ketocarboxylic Acids with Trifluoropyruvates
    Kawanishi, Ryouta
    Hattori, Shinya
    Iwasa, Seiji
    Shibatomi, Kazutaka
    MOLECULES, 2019, 24 (15):
  • [6] Amine-Catalyzed Direct Photoarylation of Unactivated Arenes
    Zheng, Xingliang
    Yang, Luo
    Du, Weiyuan
    Ding, Aishun
    Guo, Hao
    CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (02) : 439 - 442
  • [7] Amine-catalyzed addition of azide ion to α,β-unsaturated carbonyl compounds
    Guerin, DJ
    Horstmann, TE
    Miller, SJ
    ORGANIC LETTERS, 1999, 1 (07) : 1107 - 1109
  • [8] CONCERNING AMINE-CATALYZED ADDITION OF TRICHLOROSILANE TO PHENYLACETYLENE . STRUCTURE OF DIADDUCT
    BENKESER, RA
    DUNNY, S
    JONES, PR
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1965, 4 (04) : 338 - &
  • [9] Construction of three contiguous stereocenters through amine-catalyzed asymmetric aldol reactions
    Hikawa, Ryoga
    Shimogaki, Mio
    Kano, Taichi
    CHEMICAL COMMUNICATIONS, 2023, 59 (54) : 8424 - 8427
  • [10] Simple highly modular acyclic amine-catalyzed direct enantioselective addition of ketones to nitro-olefins
    Xu, YM
    Córdova, A
    CHEMICAL COMMUNICATIONS, 2006, (04) : 460 - 462
12345