1605-45-4Relevant academic research and scientific papers
Cu(I)-Catalyzed Intramolecular Tandem Cyclization of N-Indole-Tethered Cyclopropenes: Synthesis of Functionalized Hydrogenated Diazabenzo[ a]cyclopenta[ cd]azulene Derivatives
Li, Peng-Hua,Yang, Song,Hao, Tong-Gang,Xu, Qin,Shi, Min
supporting information, (2019/05/07)
A Cu(I)-catalyzed [3 + 2] intramolecular cycloaddition reaction of N-indole-tethered cyclopropenes is presented in this paper. This reaction starts from the formation of ?-allyl cationic intermediate or its resonance-stabilized metal carbenoid intermediate upon activation of cyclopropene with Cu(I) catalyst and a Friedel-Crafts-type cyclization to give functionalized hydrogenated diazabenzo[a]cyclopenta[cd]azulenes in good to excellent yields along with moderate to good dr values. The asymmetric variant of this cycloaddition reaction can be realized, giving the desired products with moderate ee values.
Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics
Drew, Melanie A.,Arndt, Sebastian,Richardson, Christopher,Rudolph, Matthias,Hashmi, A. Stephen K.,Hyland, Christopher J. T.
supporting information, p. 13971 - 13974 (2019/11/25)
Cyclopropenylmethyl sulfonamides with tethered heteroaromatics have been demonstrated to undergo divergent gold-catalysed cyclisation reactions. A formal dearomative (4+3) cycloaddition takes place with furan-tethered substrates, yielding densely functionalised 5,7-fused heterocycles related to the bioactive curcusone natural products. Indole-tethered substrates display divergent reactivity giving biologically important tetrahydro-β-carbolines via a Friedel-Crafts mechanism.
RhI-Catalyzed Carbonylative [3+1] Construction of Cyclobutenones via C?C σ-Bond Activation of Cyclopropenes
Xu, Wen-Bin,Li, Changkun,Wang, Jianbo
supporting information, p. 15786 - 15790 (2018/10/15)
With a catalytic amount of Rh(cod)2BF4 and dppm, cyclopropenes undergo a direct carbonylative [3+1] cycloaddition reaction under an atmosphere of CO to produce the cyclobutenones in excellent yields, in which the regio- and diastereoselectivities can be controlled in certain cases with the help of chelating groups. Cyclobutenone with a chiral 4-position was prepared by diastereoselective induction. Rhodacyclopentenone has been determined as the key intermediate, as it was synthesized and applied to the reductive elimination step.
Rh(I)-catalyzed carbonylative carbocyclization of tethered ene- and yne-cyclopropenes
Li, Changkun,Zhang, Hang,Feng, Jiajie,Zhang, Yan,Wang, Jianbo
supporting information; experimental part, p. 3082 - 3085 (2010/08/20)
Rh(I)-catalyzed carbonylative carbocyclization of ene- and yne-cyclopropene systems provides cyclohexenones and phenols with high efficiency, respectively.
Gold(I)-catalyzed cycloisomerization of enynes containing cyclopropenes
Li, Changkun,Zeng, Yi,Zhang, Hang,Feng, Jiajie,Zhang, Yan,Wang, Jianbo
supporting information; experimental part, p. 6413 - 6417 (2010/11/19)
Goldenyne: Gold-catalyzed cycloisomerization reactions of propargyl cyclopropenes afford benzene derivatives in a highly efficient manner. The reaction either proceeds through a mechanism with or without double and triple bond cleavage, depending on the substituents (see scheme). Copyright
Structural Effects on the RhII-Catalyzed Rearrangement of Cyclopropenes
Mueller, Paul,Graenicher, Christian
, p. 521 - 534 (2007/10/02)
The termocatalytic rearrangement of 2-alkylcycloprop-2-ene-1-carboxylates (1) in the presence of RhII perfluorobutyrate is regio- and stereospecific and leads to the less substituted metallocarbenes 3.The latter undergo intramolecular C-H bond insertion to form cyclopentylidenes (4).In contrast, the metallocarbenes 19, derived from 2,3-dialkylcycloprop-2-ene-1-carboxylates 6c, d, react to dienes (Z)-20, via 1,2-H migration.The cyclopropenedicarboxylates 10, in turn, rearrange exclusively to the more substituted metallocarbene 26, which cyclize to furans 28.With 6e and 12, products derived from both modes of ring-opening are observed.
