Tandem multi-step synthesis of C-carboxyazlactones promoted by N-heterocyclic carbenes

被引:40
作者
Campbell, Craig D. [1 ]
Duguet, Nicolas [1 ]
Gallagher, Katherine A. [1 ]
Thomson, Jennifer E. [1 ]
Lindsay, Anita G. [2 ]
O'Donoghue, AnnMarie C. [2 ]
Smith, Andrew D. [1 ]
机构
[1] Univ St Andrews, EaStCHEM, Sch Chem, St Andrews KY16 9ST, Fife, Scotland
[2] Univ Durham, Dept Chem, Univ Sci Labs, Durham DH1 3LE, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1039/b806816j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cascade reaction sequences incorporating N-heterocyclic carbene-based organocatalysis have been developed that allow the direct preparation of a range of (+/-)-4-phenoxycarbonylazlactones in good isolated yields (66-84%) from the corresponding N-p-anisoyl amino acids.
引用
收藏
页码:3528 / 3530
页数:3
相关论文
共 43 条
  • [1] Formation and stability of N-heterocyclic carbenes in water:: The carbon acid pKa of imidazollum cations in aqueous solution
    Amyes, TL
    Diver, ST
    Richard, JP
    Rivas, FM
    Toth, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) : 4366 - 4374
  • [2] Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot Sila-Stetter/Paal-Knorr strategy
    Bharadwaj, AR
    Scheidt, KA
    [J]. ORGANIC LETTERS, 2004, 6 (14) : 2465 - 2468
  • [3] 4-(DIMETHYLAMINO)PYRIDINE AS A CATALYST FOR CARBON ACYLATION .2. CONTROL OF CARBON VS OXYGEN ACYLATION IN BENZOFURANONES
    BLACK, TH
    ARRIVO, SM
    SCHUMM, JS
    KNOBELOCH, JM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (24) : 5425 - 5430
  • [4] Stable carbenes
    Bourissou, D
    Guerret, O
    Gabbaï, FP
    Bertrand, G
    [J]. CHEMICAL REVIEWS, 2000, 100 (01) : 39 - 91
  • [5] CHEN FMF, 1988, INT J PEPT PROT RES, V31, P339
  • [6] Dalko PI, 2001, ANGEW CHEM INT EDIT, V40, P3726, DOI 10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO
  • [7] 2-D
  • [8] In the golden age of organocatalysis
    Dalko, PI
    Moisan, L
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) : 5138 - 5175
  • [9] Tandem [4+2]/[3+2] cycloadditions of nitroalkenes
    Denmark, SE
    Thorarensen, A
    [J]. CHEMICAL REVIEWS, 1996, 96 (01) : 137 - 165
  • [10] N-Heterocyclic carbene catalysed β-lactam synthesis
    Duguet, Nicolas
    Campbell, Craig D.
    Slawin, Alexandra M. Z.
    Smith, Andrew D.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (06) : 1108 - 1113