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
  • [41] Rh-Catalyzed Aldehyde-Aldehyde Cross-Aldol Reaction under Base-Free Conditions: In Situ Aldehyde-Derived Enolate Formation through Orthogonal Activation
    Lin, Luqing
    Yamamoto, Kumiko
    Matsunaga, Shigeki
    Kanai, Motomu
    CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (12) : 2974 - 2983
  • [42] Stereoselective synthesis of the C(1)-C(12) fragments of tedanolides -: Application of a syn-selective tin(II)-mediated aldol reaction and a convertible methoxybenzyl protecting group
    Matsui, K
    Zheng, BZ
    Kusaka, S
    Kuroda, M
    Yoshimoto, K
    Yamada, H
    Yonemitsu, O
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (19) : 3615 - 3624
  • [43] Lithium acetate-catalyzed crossed aldol reaction between aldehydes and trimethylsilyl enolates generated from other aldehydes
    Kawano, Y
    Fujisawa, H
    Mukaiyama, T
    CHEMISTRY LETTERS, 2005, 34 (04) : 614 - 615
  • [44] The reaction between phenylnitromethanes and enoate derived from D-mannitol in the presence of TBAF or DBU.: Tandem SYN-selective conjugate addition and Nef reaction
    Dias, Ayres G.
    Pinho, Vagner D.
    Costa, Paulo R. R.
    QUIMICA NOVA, 2008, 31 (04): : 832 - 836
  • [45] A syn-Selective Aza-Aldol Reaction of Boron Aza-Enolates Generated from N-Sulfonyl-1,2,3-Triazoles and 9-BBN-H
    Miura, Tomoya
    Nakamuro, Takayuki
    Miyakawa, Sho
    Murakami, Masahiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (30) : 8732 - 8735
  • [46] Zwitterionic-type molten salt-catalyzed syn-selective aza-Henry reaction: solvent-free one-pot synthesis of β-nitroamines
    Kundu, Dhiman
    Debnath, Rajib Kumar
    Majee, Adinath
    Hajra, Alakananda
    TETRAHEDRON LETTERS, 2009, 50 (50) : 6998 - 7000
  • [47] syn-Selective Asymmetric Mannich Reaction of Sulfonyl Imines with Iminoesters Catalyzed by the N,N,N-Tridentate Bis(imidazolidine)pyridine (PyBidine)-Cu(OTf)2 Complex
    Arai, Takayoshi
    Mishiro, Asami
    Matsumura, Eri
    Awata, Atsuko
    Shirasugi, Mayu
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (36) : 11219 - 11222
  • [48] Recoverable PEG-supported amino alcohol ligand for copper-catalyzed Enantio- and syn-selective henry reaction with nitroethanol: Sustainable and straightforward access to chiral syn-2-nitro-1,3-Diols
    Xia, Yingqi
    Ning, Yingtang
    Liu, Minjie
    Chen, Fen -Er
    JOURNAL OF CATALYSIS, 2023, 417 : 35 - 40
  • [49] Lewis base-catalyzed anti-selective Mannich-type reaction between trimethylsilyl enolates and aldimines
    Takahashi, E
    Fujisawa, H
    Mukaiyama, T
    CHEMISTRY LETTERS, 2005, 34 (01) : 84 - 85
  • [50] anti-Selective asymmetric synthesis of β-hydroxy-α-amino acid esters by the in situ generated chiral quaternary ammonium fluoride-catalyzed Mukaiyama-type aldol reaction
    Ooi, T
    Taniguchi, M
    Doda, K
    Maruoka, K
    ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) : 1073 - 1076
12345