Reusable and highly enantioselective water-soluble Ru(II)-Amm-Pheox catalyst for intramolecular cyclopropanation of diazo compounds

被引：5
|
作者：
Mandour, Hamada S. A. [1 ]
Nakagawa, Yoko [2 ]
Tone, Masaya [2 ]
Inoue, Hayato [2 ]
Otog, Nansalmaa [2 ]
Fujisawa, Ikuhide [2 ]
Chanthamath, Soda [2 ]
Iwasa, Seiji [2 ]
机构：
[1] Tanta Univ, Dept Chem, Fac Sci, Tanta 31527, Egypt
[2] Toyohashi Univ Technol, Dept Environm & Life Sci, 1-1 Hibarigaoka,Tempaku Cho, Toyohashi, Aichi 4418580, Japan
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 15卷
基金：
日本学术振兴会;
关键词：
asymmetric synthesis; carbene transfer; cyclopropanation; diazoester; intramolecular diazoamide; Ru(II)-Pheox; water-soluble catalyst; Weinreb amide; WEINREB AMIDES; ORGANIC-REACTIONS; N-METHYLAMIDES; AQUEOUS-MEDIA; COMPLEXES; RUTHENIUM; CHEMISTRY; ALDEHYDES; OPPORTUNITIES; ACCELERATION;
D O I：
10.3762/bjoc.15.31
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A reusable and highly enantioselective catalyst for the intramolecular cyclopropanation of various diazo ester and Weinreb amide derivatives was developed. The reactions catalyzed by a water-soluble Ru(II)-Amm-Pheox catalyst proceeded smoothly at room temperature, affording the corresponding bicyclic cyclopropane ring-fused lactones and lactams in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee). After screening of various catalysts, the Ru(II)-Amm-Pheox complex having an ammonium group proved to be crucial for the intramolecular cyclopropanation reaction in a water/ether biphasic medium. The water-soluble catalyst could be reused at least six times with little loss in yield and enantioselectivity.
引用
收藏
页码：357 / 363
页数：7
相关论文
共 17 条
  • [1] Highly stereoselective cyclopropanation of diazo Weinreb amides catalyzed by chiral Ru(II)-Amm-Pheox complexes
    Chanthamath, Soda
    Mandour, Hamada S. A.
    Thu Minh Thi Tong
    Shibatomi, Kazutaka
    Iwasa, Seiji
    CHEMICAL COMMUNICATIONS, 2016, 52 (50) : 7814 - 7817
  • [2] Water-Soluble Chiral Ruthenium(II) Phenyloxazoline Complex: Reusable and Highly Enantioselective Catalyst for Intramolecular Cyclopropanation Reactions
    Abu-Elfotoh, Abdel-Moneim
    Diem Phuong Thi Nguyen
    Chanthamath, Soda
    Phomkeona, Kesiny
    Shibatomi, Kazutaka
    Iwasa, Seiji
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (18) : 3435 - 3439
  • [3] Inter- and Intramolecular Cyclopropanations of Diazo Weinreb Amides Catalyzed by Ruthenium(II)-Amm-Pheox
    Mandour, Hamada S. A.
    Chanthamath, Soda
    Shibatomi, Kazutaka
    Iwasa, Seiji
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (10) : 1742 - 1746
  • [4] Highly enantioselective intramolecular cyclopropanation of alkenyl diazo ketones using Ru(salen) as catalyst
    Saha, B
    Uchida, T
    Katsuki, T
    CHEMISTRY LETTERS, 2002, (08) : 846 - 847
  • [5] Computational chemical analysis of Ru(II)-Pheox-catalyzed highly enantioselective intramolecular cyclopropanation reactions
    Nakagawa, Yoko
    Nakayama, Naofumi
    Goto, Hitoshi
    Fujisawa, Ikuhide
    Chanthamath, Soda
    Shibatomi, Kazutaka
    Iwasa, Seiji
    CHIRALITY, 2019, 31 (01) : 52 - 61
  • [6] Computational chemical analysis for Ru(II)-Pheox catalyzed enantioselective intramolecular cyclopropanation
    Nakagawa, Yoko
    Chanthamath, Soda
    Nakayama, Naofumi
    Gotoh, Hitoshi
    Shibatomi, Kazutaka
    Iwasa, Seiji
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [7] Highly Enantioselective Synthesis of Cyclopropylamine Derivatives via Ru(II)-Pheox-Catalyzed Direct Asymmetric Cyclopropanation of Vinylcarbamates
    Chanthamath, Soda
    Dao Thi Nguyen
    Shibatomi, Kazutaka
    Iwasa, Seiji
    ORGANIC LETTERS, 2013, 15 (04) : 772 - 775
  • [8] Highly Regio- and Stereoselective Synthesis of Alkylidenecyclopropanes via Ru(II)-Pheox Catalyzed Asymmetric Inter- and Intramolecular Cyclopropanation of Allenes
    Chanthamath, Soda
    Chua, Hao Wei
    Kimura, Seiya
    Shibatomi, Kazutaka
    Iwasa, Seiji
    ORGANIC LETTERS, 2014, 16 (12) : 3408 - 3411
  • [9] Regio- and Enantioselective Intramolecular Amide Carbene Insertion into Primary C-H Bonds Using Ru(II)-Pheox Catalyst
    Nakagawa, Yoko
    Chanthamath, Soda
    Liang, Yumeng
    Shibatomi, Kazutaka
    Iwasa, Seiji
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (05): : 2607 - 2618
  • [10] A highly regio-, diastereo- and enantioselective intramolecular cyclopropanation reaction of a racemic α-diazo ketone catalyzed by chiral ortho-metalated dirhodium(II) compounds
    Pérez-Prieto, J
    Stiriba, SE
    Moreno, E
    Lahuerta, P
    TETRAHEDRON-ASYMMETRY, 2003, 14 (07) : 787 - 790
12