Highly stereoselective cyclopropanation of diazo Weinreb amides catalyzed by chiral Ru(II)-Amm-Pheox complexes

被引：25
作者：
Chanthamath, Soda [1 ]
Mandour, Hamada S. A. [1 ]
Thu Minh Thi Tong [1 ]
Shibatomi, Kazutaka [1 ]
Iwasa, Seiji [1 ]
机构：
[1] Toyohashi Univ Technol, Dept Environm & Life Sci, 1-1 Hibarigaoka,Tempaku Cho, Toyohashi, Aichi 4418580, Japan
来源：
CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 50期
基金：
日本学术振兴会;
关键词：
ASYMMETRIC CYCLOPROPANATION; INTRAMOLECULAR CYCLOPROPANATION; DIASTEREOSELECTIVE CYCLOPROPANATION; N-METHYLAMIDES; OLEFINS; EFFICIENT; SYSTEMS; DERIVATIVES; REDUCTION; ARYLATION;
D O I：
10.1039/c6cc02498j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The first highly stereoselective cyclopropanation of diazo Weinreb amides with olefins was accomplished using chiral Ru(II)-Amm-Pheox complex 7a to give the corresponding chiral cyclopropyl Weinreb amides in high yields (up to 99%) with excellent diastereoselectivities (up to 99:1 dr) and enantioselectivities (up to 96% ee).
引用
收藏
页码：7814 / 7817
页数：4
相关论文
共 54 条
  • [1] 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
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (18) : 3435 - 3439
  • [2] Asymmetric Inter- and Intramolecular Cyclopropanation Reactions Catalyzed by a Reusable Macroporous-Polymer-Supported Chiral Ruthenium(II)/Phenyloxazoline Complex
    Abu-Elfotoh, Abdel-Moneim
    Phomkeona, Kesiny
    Shibatomi, Kazutaka
    Iwasa, Seiji
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (45) : 8439 - 8443
  • [3] Catalytic sulfur ylide reactions: Use of diazoacetamides for the diastereoselective synthesis of glycidic amides.
    Aggarwal, VK
    Blackburn, P
    Fieldhouse, R
    Jones, RVH
    [J]. TETRAHEDRON LETTERS, 1998, 39 (46) : 8517 - 8520
  • [4] Reduction of Weinreb amides to aldehydes under ambient conditions with magnesium borohydride reagents
    Bailey, Christopher L.
    Clary, Jacob W.
    Tansakul, Chittreeya
    Klabunde, Lucas
    Anderson, Christopher L.
    Joh, Alexander Y.
    Lill, Alexander T.
    Peer, Natalie
    Braslau, Rebecca
    Singaram, Bakthan
    [J]. TETRAHEDRON LETTERS, 2015, 56 (05) : 706 - 709
  • [5] Vinyl Weinreb amides: a versatile alternative to vinyl ketone substrates for the Heck arylation
    Baker, David B.
    Gallagher, Peter T.
    Donohoe, Timothy J.
    [J]. TETRAHEDRON, 2013, 69 (18) : 3690 - 3697
  • [6] Natural occurrence, syntheses, and applications of cyclopropyl-group-containing α-amino acids.: 1.: 1-aminocyclopropanecarboxylic acid and other 2,3-methanoamino acids
    Brackmann, Farina
    de Meijere, Armin
    [J]. CHEMICAL REVIEWS, 2007, 107 (11) : 4493 - 4537
  • [7] 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
    [J]. ORGANIC LETTERS, 2014, 16 (12) : 3408 - 3411
  • [8] Highly Stereoselective Synthesis of Cyclopropylphosphonates Catalyzed by Chiral Ru(II)-Pheox Complex
    Chanthamath, Soda
    Ozaki, Seiya
    Shibatomi, Kazutaka
    Iwasa, Seiji
    [J]. ORGANIC LETTERS, 2014, 16 (11) : 3012 - 3015
  • [9] Highly Stereoselective Cyclopropanation of α,β-Unsaturated Carbonyl Compounds with Methyl (Diazoacetoxy) acetate Catalyzed by a Chiral Ruthenium(II) Complex
    Chanthamath, Soda
    Takaki, Suguru
    Shibatomi, Kazutaka
    Iwasa, Seiji
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (22) : 5818 - 5821
  • [10] 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
    [J]. ORGANIC LETTERS, 2013, 15 (04) : 772 - 775
123456