Catalytic Asymmetric Darzens and Aza-Darzens Reactions for the Synthesis of Chiral Epoxides and Aziridines

被引:27
作者
de los Santos, Jesus M. [1 ]
Ochoa de Retana, Ana M. [1 ]
Martinez de Marigorta, Edorta [1 ]
Vicario, Javier [1 ]
Palacios, Francisco [1 ]
机构
[1] Univ Pais Vasco UPV EHU, Dept Quim Organ 1, Fac Quim, Ctr Invest & Estudios Avanzados Lucio Lascaray, Paseo Univ 7, Vitoria 01006, Spain
关键词
aza-Darzens reaction; aziridines; Darzens reaction; epoxides; catalytic asymmetric synthesis; BOND-FORMING REACTIONS; PHASE-TRANSFER; ENANTIOSELECTIVE SYNTHESIS; AZACROWN ETHERS; D-GLUCOSE; EFFICIENT SYNTHESIS; CROWN CATALYSTS; GLYCIDIC AMIDES; GENERAL-METHOD; IMINES;
D O I
10.1002/cctc.201801026
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
This review presents an overview on the recent advances in the catalytic enantioselective Darzens and aza-Darzens reactions for the synthesis of enantiopure three-membered oxygen and nitrogen containing heterocycles. Since the synthesis of epoxides is the most widely explored, compared to their nitrogen counterparts, particularly true when asymmetric synthesis are considered, in the last decades several methodologies have appeared or improved and are now available for the preparation of aziridines in a highly stereo- and enantioselective manner. Catalytic asymmetric Darzens and aza-Darzens reaction constitute an important tool in modern organic chemistry, as there is an increased interest in bioactive natural products and pharmaceutical agents that contain these skeletons.
引用
收藏
页码:5092 / 5114
页数:23
相关论文
共 118 条
[1]   Enantio- and diastereoselective Darzens condensations [J].
Achard, Thierry J. R. ;
Belokon', Yuri N. ;
Ilyin, Michael ;
Moskalenko, Margarita ;
North, Michael ;
Pizzato, Francesca .
TETRAHEDRON LETTERS, 2007, 48 (17) :2965-2969
[2]   Effect of sulfide structure on enantioselectivity in catalytic asymmetric epoxidation of aldehydes: Mechanistic insights and implications [J].
Aggarwal, VK ;
Charmant, J ;
Dudin, L ;
Porcelloni, M ;
Richardson, J .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5467-5471
[3]  
Aggarwal VK, 1998, SYNLETT, P329
[4]   Asymmetric sulfur ylide mediated aziridination: Application in the synthesis of the side chain of taxol [J].
Aggarwal, VK ;
Vasse, JL .
ORGANIC LETTERS, 2003, 5 (21) :3987-3990
[5]   Scope and limitations in sulfur ylide mediated catalytic asymmetric aziridination of imines: use of phenyldiazomethane, diazoesters and diazoacetamides [J].
Aggarwal, VK ;
Ferrara, M ;
O'Brien, CJ ;
Thompson, A ;
Jones, RVH ;
Fieldhouse, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (14) :1635-1643
[6]  
Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1433, DOI 10.1002/1521-3773(20010417)40:8<1433::AID-ANIE1433>3.0.CO
[7]  
2-E
[8]   Novel catalytic and asymmetric process for aziridination mediated by sulfur ylides [J].
Aggarwal, VK ;
Thompson, A ;
Jones, RVH ;
Standen, MCH .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) :8368-8369
[9]   Enantioselective Aza-Darzens Reaction Catalyzed by A Chiral Phosphoric Acid [J].
Akiyama, Takahiko ;
Suzuki, Tohru ;
Mori, Keiji .
ORGANIC LETTERS, 2009, 11 (11) :2445-2447
[10]  
Annunziata R., 1979, SYNTHETIC COMMUN, P171