Catalytic Enantioselective Addition of Thioacids to Trisubstituted Nitroalkenes

被引：37
作者：
Phelan, James P. [1 ]
Patel, Evan J. [1 ]
Ellman, Jonathan A. [1 ]
机构：
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 42期
关键词：
asymmetric catalysis; michael addition; nitroalkene; organocatalysis; MICHAEL ADDITION; THIOACETIC ACID; DRUG DISCOVERY; DERIVATIVES; OXETANES; MALONATE; ANALOGS;
D O I：
10.1002/anie.201406971
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The first example of a catalytic enantioselective addition to and nitronate protonation of trisubstituted nitroalkenes to produce highly enantioenriched products with a tetrasubstituted carbon is reported. Thioacids added in excellent yields and with high enantioselectivities to both activated and unactivated nitroalkenes. The 1,2-nitrothioacetate products can be readily converted in two steps to biomedically relevant 1,2-aminosulfonic acids without loss of enantiopurity.
引用
收藏
页码：11329 / 11332
页数：4
相关论文
共 38 条
  • [11] Asymmetric organocatalytic domino reactions
    Enders, Dieter
    Grondal, Christoph
    Huettl, Matthias R. M.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) : 1570 - 1581
  • [12] Asymmetric sulfa-Michael additions
    Enders, Dieter
    Luettgen, Karsten
    Narine, Arun A.
    [J]. SYNTHESIS-STUTTGART, 2007, (07): : 959 - 980
  • [13] Quaternary ammonium N,N-dichloroamines as topical, antimicrobial agents
    Francavilla, Charles
    Low, Eddy
    Nair, Satheesh
    Kim, Bum
    Shiau, Timothy P.
    Debabov, Dmitri
    Celeri, Chris
    Alvarez, Nichole
    Houchin, Ashley
    Xu, Ping
    Najafi, Ron
    Jain, Rakesh
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (10) : 2731 - 2734
  • [14] Bicyclic guanidine-catalyzed enantioselective phospha-Michael reaction:: synthesis of chiral β-aminophosphine oxides and β-aminophosphines
    Fu, Xiao
    Jiang, Zhiyong
    Tan, Choon-Hong
    [J]. CHEMICAL COMMUNICATIONS, 2007, (47) : 5058 - 5060
  • [15] Catalytic Enantioselective Protonation of Nitronates Utilizing an Organocatalyst Chiral Only at Sulfur
    Kimmel, Kyle L.
    Weaver, Jimmie D.
    Lee, Melissa
    Ellman, Jonathan A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (22) : 9058 - 9061
  • [16] Enantio- and diastereoselective addition of cyclohexyl Meldrum's acid to β- and α,β-disubstituted nitroalkenes via N-sulfinyl urea catalysis
    Kimmel, Kyle L.
    Weaver, Jimmie D.
    Ellman, Jonathan A.
    [J]. CHEMICAL SCIENCE, 2012, 3 (01) : 121 - 125
  • [17] Enantioselective Addition of Thioacetic Acid to Nitroalkenes via N-Sulfinyl Urea Organocatalysis
    Kimmel, Kyle L.
    Robak, MaryAnn T.
    Ellman, Jonathan A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (25) : 8754 - +
  • [18] KOBAYASHI J, 1995, TETRAHEDRON, V51, P10487
  • [19] Asymmetric Michael addition of arylthiols to α,β-unsaturated carbonyl compounds catalyzed by bifunctional organocatalysts
    Li, BJ
    Jiang, L
    Liu, M
    Chen, YC
    Ding, LS
    Wu, Y
    [J]. SYNLETT, 2005, (04) : 603 - 606
  • [20] HALICYLINDRAMIDES A-C, ANTIFUNGAL AND CYTOTOXIC DEPSIPEPTIDES FROM THE MARINE SPONGE HALICHONDRIA-CYLINDRATA
    LI, HY
    MATSUNAGA, S
    FUSETANI, N
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (02) : 338 - 343
1234