57210-38-5Relevant academic research and scientific papers
One-Pot Access to 1,7a-Dihydro-1,3a-ethano-indene and 1,8a-Dihydro-1,3a-ethano-azulene Skeletons by a Sequential Gold(I)-Catalyzed Propargyl Claisen Rearrangement/Nazarov Cyclization/[4+2] Cycloaddition Reaction
Langé, Vittoria,Occhiato, Ernesto G.,Rinaldi, Antonia,Scarpi, Dina
, p. 5078 - 5086 (2020)
An efficient synthetic approach to the tricyclic 1,7a-dihydro-1,3a-ethano-indene and 1,8a-dihydro-1,3a-ethano-azulene skeletons from suitable propargyl vinyl ethers is based on a one-pot, multistep process entailing a gold(I)-catalyzed propargyl Claisen rearrangement/Nazarov cyclization, a [4+2] cycloaddition of the formed six-or seven-membered ring-fused cyclopentadiene system, and a final protection step for the easy isolation and purification of the products by chromatography.
Ti-catalyzed regioselective ring-opening alkynylation of epoxides with haloalkynes
Zhang, Di,Li, Hao,Yi, Dong,Tu, Shijing,Qi, Zhongyu,Wei, Siping,Fu, Qiang,Fu, Haiyan,Du, Xi
supporting information, (2021/11/01)
Ti-catalyzed ring-opening alkynylation of epoxides with haloalkynes has been achieved, allowing an efficient and regioselective entry to various propargylic alcohols in moderate to good yields. The developed protocol features extremely mild reaction conditions, broad substrate scope, varied functional group compatibility, and chemospecificity in the rearrangements of epoxides to aldehydes.
Preparation of substituted cyclopentadienes through platinum(II)-catalyzed cyclization of 1,2,4-trienes
Funami, Hideaki,Kusama, Hiroyuki,Iwasawa, Nobuharu
, p. 909 - 911 (2007/10/03)
(Chemical Equation Presented) A pinch of platinum... Platinum(II)-catalyzed cyclization of 1,2,4-trienes proceeds under mild conditions to give well-defined, highly substituted cyclopentadienes in good yield. The reaction was confirmed to proceed through
Synthesis of trisubstituted furans from epoxypropargyl esters by sequential SmI2-promoted reduction - Elimination and Pd(II)-catalyzed cycloisomerization
Aurrecoechea,Perez,Solay
, p. 564 - 569 (2007/10/03)
A two-step one-pot synthesis of 2,3,5-trisubstituted furans 8 from 4,5-epoxyalk-2-ynyl esters 6 is described. The sequence is initiated by a SmI2-promoted reduction that takes advantage of the ability of the alkynyloxirane moiety present in 6 to accept electrons from SmI2. The resulting organosamarium species then eliminates an adjacent acetate or benzoate leaving group, leading to the formation of unstable 2,3,4-trien-1-ols 7. Without isolation, these are cycloisomerized to furans 8 by treatment with a catalytic amount of a Pd(II) complex and a proton source. The whole sequence takes place under mild reaction conditions. Some useful functional groups such as cyano and α, βunsaturated esters are tolerated, but benzyl- and silyl-protected hydroxyl groups are deprotected to some extent. Starting materials can be easily assembled using reliable reactions from acetylene, an aldehyde or ketone, and a vinyl halide fragment. This offers the possibility of introducing branched substituents at C-5 of the furan ring.
