Bifunctional Reactivity of CuI: Sequential Ring Opening/N-Arylation

被引:36
作者
Martins, Andrew [1 ]
Lemouzy, Sebastien [1 ]
Lautens, Mark [1 ]
机构
[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada
关键词
PALLADIUM-CATALYZED REACTIONS; MESO BICYCLIC HYDRAZINES; STEREOSELECTIVE-SYNTHESIS; FACILE SYNTHESIS; BOND FORMATION; N-ARYLATION; ONE-POT; CYCLOPENTENES; DESYMMETRIZATION; DIAZABICYCLES;
D O I
10.1021/ol802357e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The sequential use of a single Cut catalyst enables the one-pot synthesis of N-arylaminooxazolidinones through a Lewis acid catalyzed rearrangement followed by an N-arylation reaction. Contrary to previous reports, the formation of a cis-fused 5,5-membered ring system occurs during the rearrangement, as proven by X-ray crystallography.
引用
收藏
页码:181 / 183
页数:3
相关论文
共 27 条
  • [1] ALEXAKIS A, 2002, EUR J ORG CHEM, V322, P1
  • [2] Palladium/Lewis acid catalyzed desymmetrization of fulvene-derived bicyclic hydrazines: A facile synthesis of substituted alkylidene cyclopentenes
    Anas, S.
    Sajisha, V. S.
    Mohanlal, Smitha
    Radhakrishnan, K. V.
    [J]. SYNLETT, 2006, (15) : 2399 - 2402
  • [3] Copper catalyzed allylic oxidation with peresters
    Andrus, MB
    Lashley, JC
    [J]. TETRAHEDRON, 2002, 58 (05) : 845 - 866
  • [4] Highly functionalized cyclopentanes from meso bicyclic hydrazines. A rapid access to mannosidase inhibitors
    Bournaud, C
    Robic, D
    Bonin, M
    Micouin, L
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) : 3316 - 3317
  • [5] Heterocycle synthesis by copper facilitated addition of heteroatoms to alkenes, alkynes and arenes
    Chemler, Sherry R.
    Fuller, Peter H.
    [J]. CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) : 1153 - 1160
  • [6] Copper-Catalyzed One-Pot Multicomponent Coupling Reaction of Phenols, Amides, and 4-Bromphenyl Iodide
    Chen, Wenming
    Li, Jianjun
    Fang, Dongimei
    Feng, Chun
    Zhang, Chenggang
    [J]. ORGANIC LETTERS, 2008, 10 (20) : 4565 - 4568
  • [7] CHUNG CYJ, 1972, CAN J CHEMISTRY, V50, P1568
  • [8] NOVEL ACID-CATALYZED ISOMERIZATION OF ADDUCTS OF 1,4-DIMETHYL-2,3-DIPHENYLCYCLOPENTADIENE AND DIALKYL AZODICARBOXYLATES
    DAO, LH
    MACKAY, D
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1978, 56 (13): : 1724 - 1728
  • [9] Recent advances in Ullmann reaction:: Copper(II) diacetate catalysed N-, O- and S-arylation involving polycoordinate heteroatomic derivatives
    Finet, JP
    Fedorov, AY
    Combes, S
    Boyer, G
    [J]. CURRENT ORGANIC CHEMISTRY, 2002, 6 (07) : 597 - 626
  • [10] Successive copper(I)-catalyzed cross-couplings in one pot: A novel and efficient starting point for synthesis of carbapenems
    Jiang, Biao
    Tian, Hua
    Huang, Zuo-Gang
    Xu, Min
    [J]. ORGANIC LETTERS, 2008, 10 (13) : 2737 - 2740