Ammonium phenoxides-catalyzed syn-selective aldol reaction between an aldehyde and an trimethylsilyl enolate

被引：10
|
作者：
Fujisawa, H
Nagata, Y
Sato, Y
Mukaiyama, T
机构：
[1] Kitasato Inst TCI, Ctr Basic Res, Kita Ku, Tokyo 1140003, Japan
[2] Kitasato Univ, Kitasato Inst Life Sci, Minato Ku, Tokyo 1088641, Japan
来源：
CHEMISTRY LETTERS | 2005年 / 34卷 / 06期
关键词：
D O I：
10.1246/cl.2005.842
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Aldol reactions between aldehydes and trimethylsilyl enolates generated from ketones or thioesters proceeded smoothly in the presence of a Lewis base catalyst such as tetrabutylammonium phenoxide or p-methoxyphenoxide in THF to afford the corresponding aldols in high yields with high syn-selectivity.
引用
收藏
页码：842 / 843
页数：2
相关论文
共 50 条
  • [21] Boron-mediated aldol reaction of carboxylic esters: Complementary anti- and syn-selective asymmetric aldol reactions
    Inoue, T
    Liu, JF
    Buske, DC
    Abiko, A
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15): : 5250 - 5256
  • [22] syn-Selective Aldol Reactions Catalyzed by Praline Methyl Ester under Solvent-Free Conditions
    Peng, Yiyuan
    Cui, Ming
    Mao, Xuechun
    Ye, Wei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2010, 30 (03) : 389 - 394
  • [23] Asymmetric syn-selective direct aldol reaction of protected hydroxyacetone catalyzed by primary amino acid derived bifunctional organocatalyst in the presence of water
    Kumar, Akshay
    Singh, Sarbjit
    Kumar, Vikas
    Chimni, Swapandeep Singh
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (08) : 2731 - 2742
  • [24] Synthesis of β-Hydroxy-α-haloesters through Super Silyl Ester Directed Syn-Selective Aldol Reaction
    Oda, Susumu
    Yamamoto, Hisashi
    ORGANIC LETTERS, 2013, 15 (23) : 6030 - 6033
  • [25] Asymmetric syn-selective Henry reaction catalyzed by the sulfonyldiamine-CuCl-pyridine system
    Arai, Takayoshi
    Takashita, Ryuta
    Endo, Yoko
    Watanabe, Masahiko
    Yanagisawa, Akira
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (13): : 4903 - 4906
  • [26] Theoretical study of stereoselectivity for syn-selective cross-aldol reactions of aldehydes catalyzed by chiral diamine organocatalysts
    Zhao, Chengyan
    Fu, Aiping
    Li, Hongliang
    Wang, Ping
    Xu, Yong
    Duan, Yunbo
    ADVANCES IN APPLIED SCIENCE AND INDUSTRIAL TECHNOLOGY, PTS 1 AND 2, 2013, 798-799 : 59 - 62
  • [27] ALDOL CONDENSATION - EFFECT OF ALKYL SUBSTITUENTS ON STEREOCHEMISTRY OF REACTION BETWEEN AN ENOLATE AND AN ALDEHYDE OR KETONE
    FELLMANN, P
    DUBOIS, JE
    TETRAHEDRON, 1978, 34 (09) : 1349 - 1357
  • [28] syn-Selective asymmetric cross-aldol reactions between aldehydes and glyoxylic acid derivatives catalyzed by an axially chiral amino sulfonamide
    Kano, Taichi
    Noishiki, Akira
    Sakamoto, Ryu
    Maruoka, Keiji
    CHEMICAL COMMUNICATIONS, 2011, 47 (38) : 10626 - 10628
  • [29] Product-catalyzed aldol reaction between trimethylsilyl enolates and aldehydes
    Fujisawa, H
    Nakagawa, T
    Mukaiyama, T
    ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) : 1241 - 1246
  • [30] Atom economic and highly syn-selective prolinamide-catalyzed cross-aldol addition of hydroxyacetone to aromatic aldehydes
    Angelici, Gaetano
    Falgiani, Annamaria
    Luppi, Gianluigi
    Kaptein, Bernard
    Broxterman, Quirinus B.
    Tomasini, Claudia
    SYNTHETIC COMMUNICATIONS, 2008, 38 (07) : 1137 - 1146
12345