N-Heterocyclic carbene-catalyzed diastereoselective synthesis of β-lactone-fused cyclopentanes using homoenolate annulation reaction

被引:24
作者
Mukherjee, Subrata [1 ]
Mondal, Santigopal [1 ]
Patra, Atanu [1 ]
Gonnade, Rajesh G. [2 ]
Biju, Akkattu T. [1 ]
机构
[1] CSIR Natl Chem Lab CSIR NCL, Div Organ Chem, Pune 411008, Maharashtra, India
[2] CSIR Natl Chem Lab CSIR NCL, Ctr Mat Characterizat, Pune 411008, Maharashtra, India
关键词
STEREOSELECTIVE-SYNTHESIS; FUNCTIONALIZED CYCLOPENTENES; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; KINETIC RESOLUTION; MICHAEL ADDITION; ENALS; ACYL; CHALCONES;
D O I
10.1039/c5cc02960k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
NHC-catalyzed annulation of enals with 2-enoylpyridines or 2-enoylpyridine N-oxides leading to the diastereoselective synthesis of beta-lactone-fused cyclopentanes is reported. The reaction proceeds via the generation of homoenolate equivalent intermediates and tolerates a broad range of functional groups.
引用
收藏
页码:9559 / 9562
页数:4
相关论文
共 62 条
  • [1] Asymmetric Synthesis of Highly Substituted β-Lactones through Oxidative Carbene Catalysis with LiCl as Cooperative Lewis Acid
    Bera, Srikrishna
    Samanta, Ramesh C.
    Daniliuc, Constantin G.
    Studer, Armido
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (36) : 9622 - 9626
  • [2] NHC-Catalyzed Reaction of Enals with Hydroxy Chalcones: Diastereoselective Synthesis of Functionalized Coumarins
    Bhunia, Anup
    Patra, Atanu
    Puranik, Vedavati G.
    Biju, Akkattu T.
    [J]. ORGANIC LETTERS, 2013, 15 (07) : 1756 - 1759
  • [3] 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
  • [4] β-Lactams and β-lactones as activity-based probes in chemical biology
    Boettcher, Thomas
    Sieber, Stephan A.
    [J]. MEDCHEMCOMM, 2012, 3 (04) : 408 - 417
  • [5] Organocatalytic umpolung: N-heterocyclic carbenes and beyond
    Bugaut, Xavier
    Glorius, Frank
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) : 3511 - 3522
  • [6] 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
  • [7] N-tert-Butyl Triazolylidenes: Catalysts for the Enantioselective (3+2) Annulation of ,-Unsaturated Acyl Azoliums
    Candish, Lisa
    Forsyth, Craig M.
    Lupton, David W.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) : 9149 - 9152
  • [8] N-Heterocyclic Carbene-Catalyzed Ireland-Coates Claisen Rearrangement: Synthesis of Functionalized β-Lactones
    Candish, Lisa
    Lupton, David W.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (01) : 58 - 61
  • [9] Cooperative N-Heterocyclic Carbene/Lewis Acid Catalysis for Highly Stereoselective Annulation Reactions with Homoenolates
    Cardinal-David, Benoit
    Raup, Dustin E. A.
    Scheidt, Karl A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (15) : 5345 - +
  • [10] Enantioselective Cycloaddition Reactions of Ketenes Catalyzed by N-Heterocyclic Carbenes
    Chen, Xiang-Yu
    Ye, Song
    [J]. SYNLETT, 2013, 24 (13) : 1614 - 1622