Halodiazophosphonates, a New Class of Diazo Compounds for the Diastereoselective Intermolecular Rh(II) Catalyzed Cyclopropanation

被引：17
|
作者：
Schnaars, Christian [1 ]
Hansen, Tore [1 ]
机构：
[1] Univ Oslo, Dept Chem, N-0315 Oslo, Norway
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 11期
关键词：
H INSERTION REACTIONS; ENANTIOSELECTIVE SYNTHESIS; DONOR/ACCEPTOR CARBENOIDS; ASYMMETRIC-SYNTHESIS; RHODIUM CARBENOIDS; CYCLOPROPYLPHOSPHONATES; ALKENES; FUNCTIONALIZATION; SELECTIVITY; ACTIVATION;
D O I：
10.1021/ol3010276
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(Halodiazomethyl)phosphonates 2A-C have been generated by a one-pot procedure via a clean, efficient, and rapid deprotonation/electrophilic halogenation sequence from diethyl diazomethylphosphonate 1 (EDP). Subsequent Intermolecular Rh(II)-catalyzed cyclopropanation afforded the corresponding halocyclopropylphosphonates 3-10 in moderate to high yields and high diastereomeric ratios. Catalyst loadings down to 0.1 mol % as well as clean and selective product formation were achieved.
引用
收藏
页码：2794 / 2797
页数：4
相关论文
共 50 条
  • [41] Saturation kinetics in dirhodium(II) carboxylate-catalyzed decompositions of diazo compounds
    Pirrung, MC
    Morehead, AT
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (34) : 8162 - 8163
  • [42] A highly regio-, diastereo- and enantioselective intramolecular cyclopropanation reaction of a racemic α-diazo ketone catalyzed by chiral ortho-metalated dirhodium(II) compounds
    Pérez-Prieto, J
    Stiriba, SE
    Moreno, E
    Lahuerta, P
    TETRAHEDRON-ASYMMETRY, 2003, 14 (07) : 787 - 790
  • [43] A Lewis Acid-Catalyzed Diastereoselective Synthesis of Functionalized 2-Diazo-1,5-dicarbonyl Compounds
    Howard, Evan M.
    Brewer, Matthias
    ACS CATALYSIS, 2021, 11 (19) : 12203 - 12207
  • [44] Rh(II)-catalyzed enantioselective cyclopropanation of olefins with dimethyl malonate via in situ generated phenyliodonium ylide
    Muller, P
    Ghanem, A
    ORGANIC LETTERS, 2004, 6 (23) : 4347 - 4350
  • [45] Diastereoselective Synthesis of γ-Substituted 2-Butenolides via (CDC)-Rh-Catalyzed Intermolecular Hydroalkylation of Dienes with Silyloxyfurans
    Goldfogel, Matthew J.
    Roberts, Courtney C.
    Manan, Rajith S.
    Meek, Simon J.
    ORGANIC LETTERS, 2017, 19 (01) : 90 - 93
  • [46] Rh(III)-Catalyzed, Highly Selectively Direct C-H Alkylation of Indoles with Diazo Compounds
    Wan, Kang
    Li, Zhan
    Qu, Xing
    Wang, Feng
    Wang, Liang
    CATALYSTS, 2016, 6 (06):
  • [47] Rh(III)-Catalyzed Redox-Neutral Annulation of Primary Benzamides with Diazo Compounds: Approach to Isoquinolinones
    Wu, Youzhi
    Sun, Peng
    Zhang, Kaifan
    Yang, Tie
    Yao, Hequan
    Lin, Aijun
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (05): : 2166 - 2173
  • [48] Cooperative Rh(II)/Pd(0) Dual-Catalyzed gem-Difunctionalization of α-Diazo Carbonyl Compounds: Construction of Quaternary Carbon Centers
    Xuan, Zi
    Chen, Zi-Sheng
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (26)
  • [49] Controllable Rh(III)-Catalyzed Annulation between Salicylaldehydes and Diazo Compounds: Divergent Synthesis of Chromones and Benzofurans
    Sun, Peng
    Gao, Shang
    Yang, Chi
    Guo, Songjin
    Lin, Aijun
    Yao, Hequan
    ORGANIC LETTERS, 2016, 18 (24) : 6464 - 6467
  • [50] Rh(III)-Catalyzed synthesis of pyrazolo[1,2-a] cinnolines from pyrazolidinones and diazo compounds
    Li, Panpan
    Xu, Xiaoying
    Chen, Jiayi
    Yao, Hequan
    Lin, Aijun
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (11): : 1777 - 1781
12345