Binaphthyl-Modified Quaternary Phosphonium Salts as Chiral Phase Transfer Catalysts: Application to Asymmetric Amination of β-Keto Esters

被引:44
|
作者
He, Rongjun [1 ]
Maruoka, Keiji [1 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
来源
SYNTHESIS-STUTTGART | 2009年 / 13期
关键词
amination; asymmetric synthesis; phase-transfer catalysis; phosphonium salts; SUBSTITUTED ALPHA-CYANOACETATES; ALDOSE REDUCTASE INHIBITOR; ELECTROPHILIC AMINATION; AS-3201; ALKYLATION;
D O I
10.1055/s-0029-1216848
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A chiral quaternary tetraatkylphosphonium salt has been successfully utilized for the first time as a phase-transfer catalyst for asymmetric amination of beta-keto esters in high yield with high ee. Asymmetric amination of a cyclic five-mernbered beta-keto ester is a valuable method for preparing a key intermediate for asymmetric synthesis of aldose reductase inhibitor AS-3201 (Ranirestat).
引用
收藏
页码:2289 / 2292
页数:4
相关论文
共 50 条
  • [1] Binaphthyl-Modiried Quaternary Phosphonium Salts as Chiral Phase-Transfer Catalysts: Asymmetric Amination of β-Keto Esters
    He, Rongjun
    Wang, Xisheng
    Hashimoto, Takuya
    Maruoka, Keiji
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (49) : 9466 - 9468
  • [2] Chiral quaternary phosphonium salts as phase-transfer catalysts for environmentally benign asymmetric transformations
    Liu, Shiyao
    Kumatabara, Yusuke
    Shirakawa, Seiji
    GREEN CHEMISTRY, 2016, 18 (02) : 331 - 341
  • [3] Asymmetric Michael Addition of Pyrazolones to ,-Unsaturated -Keto Esters Catalyzed by Binaphthyl-modified Thiourea
    Kim, You Sun
    Lee, Min Hee
    Kim, Dae Young
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2018, 39 (04): : 579 - 582
  • [4] Recent Asymmetric Phase-Transfer Catalysis with Chiral Binaphthyl-Modified and Related Phase-Transfer Catalysts over the Last 10 Years
    Lee, Hyo-Jun
    Maruoka, Keiji
    CHEMICAL RECORD, 2023, 23 (07):
  • [5] Substituent effect of binaphthyl-modified spiro-type chiral phase-transfer catalysts
    Hashimoto, T
    Maruoka, K
    TETRAHEDRON LETTERS, 2003, 44 (16) : 3313 - 3316
  • [6] Chiral bifunctional phase transfer catalysts for asymmetric fluorination of β-keto esters
    Wang, Xisheng
    Lan, Quan
    Shirakawa, Seiji
    Maruoka, Keiji
    CHEMICAL COMMUNICATIONS, 2010, 46 (02) : 321 - 323
  • [7] Highly efficient asymmetric amination of β-keto esters catalyzed by chiral quaternary ammonium bromides
    Lan, Quan
    Wang, Xisheng
    He, Rongjun
    Ding, Changhua
    Maruoka, Keiji
    TETRAHEDRON LETTERS, 2009, 50 (26) : 3280 - 3282
  • [8] Enantioselective alkylation of β-keto esters by phase-transfer catalysis using chiral quaternary ammonium salts
    Park, EJ
    Kim, MH
    Kim, DY
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (20): : 6897 - 6899
  • [9] Design of binaphthyl-modified symmetrical chiral phase-transfer catalysts:: Substituent effect of 4,4′,6,6′-positions of binaphthyl rings in the asymmetric alkylation of a glycine derivative
    Shirakawa, Seiji
    Ueda, Mitsuhiro
    Tanaka, Youhei
    Hashimoto, Takuya
    Maruoka, Keiji
    CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (10) : 1276 - 1281
  • [10] Synthesis of novel chiral quaternary phosphonium salts with a multiple hydrogen-bonding site, and their application to asymmetric phase-transfer alkylation
    Manabe, K
    TETRAHEDRON, 1998, 54 (48) : 14465 - 14476