Enantioselective Gold(I)-Catalyzed Vinylogous [3+2] Cycloaddition between Vinyldiazoacetates and Enol Ethers

被引：102
作者：
Briones, John F. [1 ]
Davies, Huw M. L. [1 ]
机构：
[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 36期
基金：
美国国家科学基金会;
关键词：
BOND FUNCTIONALIZATION; CATALYZED CYCLIZATION; CARBENE INSERTION; CYCLOPROPANATION; REACTIVITY; CYCLOISOMERIZATIONS; HYDROAMINATION; REARRANGEMENT; COMPLEXES; AU;
D O I：
10.1021/ja407179c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The reaction of vinyldiazoacetates with enol ethers catalyzed by the binuclear gold complex (R)-DTBMSegphos(AuCl)(2) activated by silver hexafluoroantimonate results in a highly enantioselective [3 + 2] cycloaddition. The [3 + 2] cycloaddition proceeds with dynamic kinetic resolution when the enol ether is a 4-substituted 1-(methoxymethylene)cyclohexane. The reaction is initiated by nucleophilic attack of the vinyl ethers at the vinylogous position of the gold vinylcarbene intermediate.
引用
收藏
页码：13314 / 13317
页数：4
相关论文
共 53 条
  • [41] Exclusive Aromatic vs Aliphatic C-H Bond Functionalization by Carbene Insertion with Gold-Based Catalysts
    Rivilla, Ivan
    Pilar Gomez-Emeterio, B.
    Fructos, Manuel R.
    Mar Diaz-Requejo, M.
    Perez, Pedro J.
    [J]. ORGANOMETALLICS, 2011, 30 (10) : 2855 - 2860
  • [42] Au(I)-catalyzed ring expanding cycloisomerizations: Total synthesis of ventricosene
    Sethofer, Steven G.
    Staben, Steven T.
    Hung, Olivia Y.
    Toste, F. Dean
    [J]. ORGANIC LETTERS, 2008, 10 (19) : 4315 - 4318
  • [43] Gold(I)-Catalyzed Enantioselective Polycyclization Reactions
    Sethofer, Steven G.
    Mayer, Timo
    Toste, F. Dean
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (24) : 8276 - +
  • [44] Influence of electron-deficient ruthenium(I) carbonyl carboxylates on the vinylogous reactivity of metal carbenoids
    Sevryugina, Yulia
    Weaver, Beth
    Hansen, Jorn
    Thompson, Janelle
    Davies, Huw M. L.
    Petrukhina, Marina A.
    [J]. ORGANOMETALLICS, 2008, 27 (08) : 1750 - 1757
  • [45] A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions
    Shapiro, Nathan D.
    Toste, F. Dean
    [J]. SYNLETT, 2010, (05) : 675 - 691
  • [46] Rhodium-Catalyzed Enantioselective Vinylogous Addition of Enol Ethers to Vinyldiazoacetates
    Smith, Austin G.
    Davies, Huw M. L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (44) : 18241 - 18244
  • [47] Trost BM, 2001, ADV SYNTH CATAL, V343, P490, DOI 10.1002/1615-4169(200107)343:5<490::AID-ADSC490>3.0.CO
  • [48] 2-S
  • [49] A CYCLOADDITION APPROACH TO CYCLOPENTENES VIA METALLADIENES AS 4-PI PARTNERS
    TROST, BM
    HASHMI, ASK
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) : 2183 - 2184
  • [50] ON THE MECHANISM OF THE TCPC(HFB)-CATALYZED METATHESIS OF 1,6-ENYNE - EVIDENCE FOR ALKYLIDENEPALLADIUM INTERMEDIATES
    TROST, BM
    HASHMI, ASK
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (07): : 1085 - 1087
123456