Catalytic Enantioselective Protonation of α-Oxygenated Ester Enolates Prepared through Phospha-Brook Rearrangement

被引：119
|
作者：
Hayashi, Masashi [1 ]
Nakamura, Shuichi [1 ]
机构：
[1] Nagoya Inst Technol, Dept Frontier Mat, Grad Sch Engn, Showa Ku, Nagoya, Aichi 4668555, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 10期
关键词：
enantioselectivity; enolates; organocatalysis; phospha-Brook rearrangement; protonation; ASYMMETRIC HYDROPHOSPHONYLATION; HYDROXY PHOSPHONATES; ACID; DERIVATIVES; KETONES; DECARBOXYLATION; ALDEHYDES; EFFICIENT; AMINO;
D O I：
10.1002/anie.201007568
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Phosphonates go chiral: The organocatalytic enantioselective reaction of α-ketoesters with phosphites using cinchona alkaloids and Na2CO3 has afforded α-phosphonyloxy esters with high enantioselectivities (see scheme). This process allows the formation of both enantiomers of the product. A catalyst loading of as low as 2 mol% does not result in a significant decrease of the enantioselectivity. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：2249 / 2252
页数：4
相关论文
共 50 条
  • [1] CATALYTIC ENANTIOSELECTIVE PROTONATION OF ENOLATES
    FEHR, C
    GALINDO, J
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (18): : 1888 - 1889
  • [2] Mechanistic insights into n-BuLi mediated phospha-Brook rearrangement
    Ranga, Santosh
    Chakravarty, Manab
    Chatterjee, Tanmay
    Ghosal, Subhas
    NEW JOURNAL OF CHEMISTRY, 2019, 43 (25) : 9886 - 9890
  • [3] Room Temperature DBN Initiated Phospha-Brook Rearrangement of α-Hydroxyphosphonates to Phosphates
    Mahandru-Gill, Muskaan
    Iqbal, Aleema
    Damai, Margarita
    Spiedo, Francesco
    Kasonde, Edward K.
    Sykes, Daniel
    Devine, Kevin G.
    Patel, Bhaven
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (43)
  • [4] Trivalent Phospha-Brook rearrangement enabled practical deoxygenative phosphonylation of carbonyls
    Xiaoqiang Wu
    Shanya Lu
    Wei Zhong
    Tao XU
    Nature Communications, 16 (1)
  • [5] HIGHLY ENANTIOSELECTIVE PROTONATION OF THIOL ESTER ENOLATES
    FEHR, C
    STEMPF, I
    GALINDO, J
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (07): : 1042 - 1044
  • [6] Continuous Flow Optimisation of the Pudovik Reaction and Phospha-Brook Rearrangement Using DBN
    Dean, Joseph
    Reinoso, Natalia Buckler
    Spiedo, Francesco
    Fernandez, Carola Romero
    Patel, Bhaven
    REACTIONS, 2024, 5 (04): : 812 - 822
  • [7] Synthesis of (Difluoromethyl)cycloalkenes from 2-Cycloalkenones by Utilizing Phospha-Brook Rearrangement
    Yamamoto, Yoshihiko
    Ishida, Yuki
    Takamizu, Yosuke
    Yasui, Takeshi
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (16) : 3739 - 3743
  • [8] Catalytic enantioselective protonation of lithium ester enolates generated by conjugate addition of arylthiolate to enoates
    Nishimura, K
    Ono, M
    Nagaoka, Y
    Tomioka, K
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (02) : 440 - 442
  • [9] Formal Umpolung Addition of Phosphites to 2-Azaaryl Ketones under Chiral Bronsted Base Catalysis: Enantioselective Protonation Utilizing [1,2]-Phospha-Brook Rearrangement
    Kondoh, Azusa
    Hirozane, Takayuki
    Terada, Masahiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (42)
  • [10] BuLi-triggered phospha-Brook rearrangement: efficient synthesis of organophosphates from ketones and aldehydes
    Pallikonda, Gangaram
    Santosh, Ranga
    Ghosal, Subhas
    Chakravarty, Manab
    TETRAHEDRON LETTERS, 2015, 56 (24) : 3796 - 3798
12345