Adventures in the Chemistry of 1,1-Diacylcyclopropanes

被引:5
作者
Langer, Peter [1 ,2 ]
机构
[1] Univ Rostock, Inst Chem, Albert Einstein Str 3a, D-18059 Rostock, Germany
[2] Katalyse Univ Rostock e V, Leibniz Inst, Albert Einstein Str 29a, D-18059 Rostock, Germany
关键词
cyclopropanes; cyclizations; dianions; regioselectivity; silyl enol ethers; DIVERSITY-ORIENTED SYNTHESIS; 1,3-BIS(SILYL ENOL ETHERS); ALKOXY-SUBSTITUTED 1,1-DIACYLCYCLOPROPANES; FORMAL 3+3 CYCLIZATIONS; ONE-POT CYCLIZATION; REGIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; DIETHYL; 2-OXOPROPYLPHOSPHONATE; ANNULATION REACTION; CHELATION CONTROL;
D O I
10.1055/s-0042-1751430
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The present personalized account aims to highlight 1,1-dia-cylcyclopropanes as synthetic building blocks or target molecules. The chemistry presented includes cyclization reactions of 1,1-diacylcyclo-propanes with free and masked dianions to give spirocyclopropanes as products or reactive intermediates that readily undergo ring-cleavage reactions. In addition, the synthesis of cyclopropylated 1,3,5-tricarbon-yl compounds, containing two 1,1-diacylcyclopropane moieties, is dis-cussed. Based on this work also other syntheses of cyclopropanes were developed.
引用
收藏
页码:1765 / 1776
页数:12
相关论文
共 63 条
  • [1] Synthesis of 4,5-benzotropones by cyclization of 1,3-bis-silyl enol ethers with 1,2-dialdehydes
    Albrecht, U
    Nguyen, THV
    Langer, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) : 3417 - 3424
  • [2] One-pot cyclization of dilithiated nitriles with isothiocyanates and epibromohydrin. Synthesis of 2-cyano-1-(hydroxymethyl)cyclopropanes and 2-cyanomethylidene-4-(hydroxymethyl)thiazolidines
    Albrecht, Uwe
    Freifeld, Ilia
    Reinke, Helmut
    Langer, Peter
    [J]. TETRAHEDRON, 2006, 62 (24) : 5775 - 5786
  • [3] Regioselective synthesis of spiro-cyclopropanated 1-aminopyrrol-2-ones by Bi(OTf)3-catalyzed one-pot 'Mukaiyama-Michael addition/cyclization/ring-contraction' reactions of 1,2-bis(trimethylsilyloxy)cyclobutene with 1,2-diaza-1,3-butadienes
    Attanas, Orazio A.
    Favi, Gianfranco
    Giorgi, Gianluca
    Mantellini, Fabio
    Karapetyan, Vahuni
    Langer, Peter
    [J]. TETRAHEDRON, 2009, 65 (28) : 5456 - 5461
  • [4] AYER WA, 1981, TETRAHEDRON, V37, P2199, DOI 10.1016/S0040-4020(01)97979-7
  • [5] Battiste M.A., 1987, CHEM CYCLOPROPYL GRO, V1, P255
  • [6] Recent advances in the chemistry of 2-(2-oxoalkylidene)tetrahydrofurans
    Bellur, Esen
    Feist, Holger
    Langer, Peter
    [J]. TETRAHEDRON, 2007, 63 (45) : 10865 - 10888
  • [7] Regioselective Synthesis of Pyrazoles and Isoxazoles with Cyclopropanated Side-Chain
    Bendrath, Franziska
    Falodun, Abiodun
    Abilov, Zharylkasyn A.
    Villinger, Alexander
    Langer, Peter
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (03) : 835 - 840
  • [8] Boger D L., 1990, J AM CHEM SOC, V112, P5832
  • [9] CC-1065 and the duocarmycins: Synthetic studies
    Boger, DL
    Boyce, CW
    Garbaccio, RM
    Goldberg, JA
    [J]. CHEMICAL REVIEWS, 1997, 97 (03) : 787 - 828
  • [10] Synthesis and evaluation of CC-1065 and duocarmycin analogues incorporating the iso-CI and iso-CBI alkylation subunits: Impact of relocation of the C-4 carbonyl
    Boger, DL
    Garbaccio, RM
    Jin, Q
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (25) : 8875 - 8891