Enantioselective and Diastereoselective Conjugate Radical Additions to -Arylidene Ketones and Lactones

被引:3
|
作者
Zhao, Changjia [1 ]
Sibi, Mukund P. [1 ]
机构
[1] North Dakota State Univ, Dept Chem & Biochem, POB 2735, Fargo, ND 58108 USA
关键词
enantioselective radical reaction; arylidene ketones and lactones; diastereoselectivity; conjugate addition; chiral salen Lewis acid; LEWIS-ACID CATALYSIS; ALPHA-AMINO RADICALS; PHOTOREDOX CATALYSIS; BRONSTED ACID; LIGANDS; ENONES;
D O I
10.1055/s-0036-1590930
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly stereoselective conjugate radical addition to arylidene ketones and lactones has been developed. The conjugate radical additions using chiral salen Lewis acids proceeds with up to 99:1 dr and 87% ee in good to excellent chemical yields.
引用
收藏
页码:2971 / 2975
页数:5
相关论文
共 50 条
  • [41] Highly Enantioselective Conjugate Additions of Aldehydes to Vinyl Sulfones
    Landa, Aitor
    Maestro, Miguel
    Masdeu, Carme
    Puente, Angel
    Vera, Silvia
    Oiarbide, Mikel
    Palomo, Claudio
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (07) : 1562 - 1565
  • [42] Free radical-mediated conjugate additions. Enantioselective synthesis of enterolactone, arctigenin and isoarctigenin.
    Sibi, P
    Hajra, S
    Liu, PR
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U76 - U76
  • [43] Calcium(II)-catalyzed enantioselective conjugate additions of amines
    Uno, Brice E.
    Dicken, Rachel D.
    Redfern, Louis R.
    Stern, Charlotte M.
    Krzywicki, Greg G.
    Scheidt, Karl A.
    CHEMICAL SCIENCE, 2018, 9 (06) : 1634 - 1639
  • [44] Nitrophenylacetonitriles as Versatile Nucleophiles in Enantioselective Organocatalytic Conjugate Additions
    Belen Cid, M.
    Duce, Sara
    Morales, Sara
    Rodrigo, Eduardo
    Garcia Ruano, Jose Luis
    ORGANIC LETTERS, 2010, 12 (16) : 3586 - 3589
  • [45] Exploration of enantioselective conjugate additions to a hindered cyclohexenone system
    Burke, Sarah J.
    Malachowski, William P.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [46] Enantioselective radical conjugate additions driven by a photoactive intramolecular iminium-ion-based EDA complex
    Zhong-Yan Cao
    Tamal Ghosh
    Paolo Melchiorre
    Nature Communications, 9
  • [47] Enantioselective radical conjugate additions driven by a photoactive intramolecular iminium-ion-based EDA complex
    Cao, Zhong-Yan
    Ghosh, Tamal
    Melchiorre, Paolo
    NATURE COMMUNICATIONS, 2018, 9
  • [48] Lactones from lactones: regio and diastereoselective double dinucleophilic additions of bis(OTMS) ketene acetals to pyridines
    Xu, Yiming
    Rudler, Henri
    Denise, Bernard
    Parlier, Andree
    Chaquin, Patrick
    Herson, Patrick
    TETRAHEDRON LETTERS, 2006, 47 (27) : 4541 - 4544
  • [49] Diastereoselective tin-free tandem radical additions
    Spatney, Russell
    Baker, Aaron
    Manpadi, Madhuri
    Zimmerman, Jake
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [50] Asymmetric synthesis of 2,3-disubstituted cyclic ketones by conjugate radical additions to unsaturated cyclic ketones: An effect of oxygen at β′ position
    Nad, Sukanya
    Sibi, Mukund P.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233