Cyclohexanones by Rh-Mediated Intramolecular C-H Insertion

被引:27
|
作者
Taber, Douglass F. [1 ]
Paquette, Craig M. [1 ]
Gu, Peiming [1 ]
Tian, Weiwei [1 ]
机构
[1] Univ Delaware, Dept Chem & Biochem, Newark, DE 19716 USA
来源
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 19期
基金
美国国家科学基金会;
关键词
CARBON-HYDROGEN INSERTION; BETA-LACTAM ANTIBIOTICS; ENANTIOSELECTIVE SYNTHESIS; CYCLOPENTANE CONSTRUCTION; MOLECULAR COMPLEXITY; ASYMMETRIC-SYNTHESIS; NATURAL-PRODUCTS; BOND ACTIVATION; DIAZO KETONES; DESIGN;
D O I
10.1021/jo4014996
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Some long chain alpha-aryl alpha-diazo ketones under Rh catalysis cyclize efficiently to the corresponding cyclohexanones. This is in marked contrast to the cyclizations of alpha-diazo beta-ketoesters, which consistently deliver cyclopentanone products.
引用
收藏
页码:9772 / 9780
页数:9
相关论文
共 50 条
  • [21] REGIOSELECTIVE RH (II) MEDIATED CARBENOID C-H INSERTION REACTIONS DICTATED BY ELECTRONIC INDUCTION
    WANG, P
    ADAMS, J
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 70 - MEDI
  • [22] MODEL STUDIES OF THE STEREOELECTRONIC EFFECT IN RH(II) MEDIATED CARBENOID C-H INSERTION REACTIONS
    WANG, P
    ADAMS, J
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) : 3296 - 3305
  • [23] Improved chemoselectivity in intramolecular alkylidene carbene C-H insertion
    Taber, DF
    Christos, TE
    TETRAHEDRON LETTERS, 1997, 38 (28) : 4927 - 4930
  • [24] Photoactivatable Fluorogens by Intramolecular C-H Insertion of Perfluoroaryl Azide
    Xie, Sheng
    Proietti, Giampiero
    Ramstrom, Olof
    Yan, Mingdi
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (22): : 14520 - 14528
  • [25] DIASTEREOSELECTIVITY IN UNCATALYZED INTRAMOLECULAR C-H INSERTION BY AN ALKYLIDENE CARBENE
    TABER, DF
    MEAGLEY, RP
    TETRAHEDRON LETTERS, 1994, 35 (43) : 7909 - 7910
  • [26] INTRAMOLECULAR C-H INSERTION IN ALKYLIDENE CARBENOIDS FOR CYCLOPENTENE DERIVATIVES
    FISCHER, RH
    BAUMANN, M
    KOBRICH, G
    TETRAHEDRON LETTERS, 1974, (13) : 1207 - 1208
  • [27] Synthesis of chiral γ-lactams via Rh(II) catalyzed intramolecular C-H insertion:: α-substituents and conformational effects
    Flanigan, DL
    Yoon, CH
    Jung, KW
    TETRAHEDRON LETTERS, 2005, 46 (01) : 143 - 146
  • [28] Rh(II) catalysed intramolecular C-H insertion of diazo substrates in water: a simple and efficient approach to catalyst reuse
    Candeias, NR
    Gois, PMP
    Afonso, CAM
    CHEMICAL COMMUNICATIONS, 2005, (03) : 391 - 393
  • [29] Regio- and stereocontrol elements in Rh(II)-catalyzed intramolecular C-H insertion of α-diazo-α-(phenylsulfonyl)acetamides
    Yoon, CH
    Zaworotko, MJ
    Moulton, B
    Jung, KW
    ORGANIC LETTERS, 2001, 3 (22) : 3539 - 3542
  • [30] Efficient Intramolecular C-H Insertion Catalyzed by Iridium Porphyrin Complexes
    Lopez-Sanchez, Cristobal
    Alvarez-Corral, Miriam
    Munoz-Dorado, Manuel
    Rodriguez-Garcia, Ignacio
    SYNLETT, 2012, (17) : 2469 - 2472