Conjugate Umpolung of β,β-Disubstituted Enals by Dual Catalysis with an N-Heterocyclic Carbene and a Bronsted Acid: Facile Construction of Contiguous Quaternary Stereocenters

被引：122
作者：
Li, Jun-Long [1 ]
Sahoo, Basudev [1 ]
Daniliuc, Constantin-G. [1 ]
Glorius, Frank [1 ]
机构：
[1] Univ Munster, Inst Organ Chem, NRW Grad Sch Chem, D-48149 Munster, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 39期
基金：
欧洲研究理事会;
关键词：
carbenes; dual catalysis; quaternary centers; spiro compounds; umpolung; GAMMA-BUTYROLACTONES; STEREOSELECTIVE-SYNTHESIS; COOPERATIVE CATALYSIS; HOMOENOLATE ADDITIONS; NATURAL-PRODUCTS; CARBON STEREOCENTERS; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; DIRECT ANNULATIONS; NHC CATALYSIS;
D O I：
10.1002/anie.201405178
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A sterically hindered homoenolate has been generated by the NHC-catalyzed conjugate umpolung of beta,beta-disubstituted enals and successfully employed in a facile stereoselective annulation with isatins. The strategy provides efficient access to spirocyclic oxindoles bearing two highly congested contiguous quaternary carbon centers. The use of a Bronsted acid cocatalyst was found to be crucial for guaranteeing both excellent reactivity and high stereoselectivity.
引用
收藏
页码：10515 / 10519
页数：5
相关论文
共 98 条
  • [1] Stronger bronsted acids
    Akiyama, Takahiko
    [J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5744 - 5758
  • [2] [Anonymous], 2007, ANGEW CHEM, DOI DOI 10.1103/PHYSREVLETT.112.077206
  • [3] [Anonymous], 2012, Angew. Chem. Int. Ed, DOI DOI 10.1002/ANGE.201106619
  • [4] Industrial natural product chemistry for drug discovery and development
    Bauer, Armin
    Broenstrupt, Mark
    [J]. NATURAL PRODUCT REPORTS, 2014, 31 (01) : 35 - 60
  • [5] Extending NHC-Catalysis: Coupling Aldehydes with Unconventional Reaction Partners
    Biju, Akkattu T.
    Kuhl, Nadine
    Glorius, Frank
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (11) : 1182 - 1195
  • [6] THE THIAZOLIUM CATALYZED BENZOIN CONDENSATION WITH MILD BASE DOES NOT INVOLVE A DIMER INTERMEDIATE
    BRESLOW, R
    KIM, R
    [J]. TETRAHEDRON LETTERS, 1994, 35 (05) : 699 - 702
  • [7] Organocatalytic umpolung: N-heterocyclic carbenes and beyond
    Bugaut, Xavier
    Glorius, Frank
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) : 3511 - 3522
  • [8] Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones
    Burstein, C
    Glorius, F
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) : 6205 - 6208
  • [9] BURSTEIN C, 2004, ANGEW CHEM, V116, P6331
  • [10] N-heterocyclic carbene-catalyzed conjugate umpolung for the synthesis of γ-butyrolactones
    Burstein, Christian
    Tschan, Serena
    Xie, Xiulan
    Glorius, Frank
    [J]. SYNTHESIS-STUTTGART, 2006, (14): : 2418 - 2439
12345678910