65351-11-3Relevant academic research and scientific papers
Highly regio- and stereoselective hydrostannylation of alkynols with a new Lewis acidic hydrostannane
Miura, Katsukiyo,Wang, Di,Matsumoto, Yukihiro,Hosomi, Akira
, p. 503 - 505 (2005)
(Chemical Equation Presented) Bu2Sn(OTf)H (1a), easily prepared from Bu2SnH2 and TfOH, was found to be very valuable for highly regio- and stereoselective hydrostannylation of various propargyl alcohols leading to (Z)-γ-st
Synthesis of 6-Substituted Piperidin-3-ones via Rh(II)-Catalyzed Transannulation of N-Sulfonyl-1,2,3-triazoles with Electron-Rich Aromatic Nucleophiles
Li, Yang,Zhang, Ran,Ali, Arshad,Zhang, Jing,Bi, Xihe,Fu, Junkai
supporting information, p. 3087 - 3090 (2017/06/23)
A highly diastereoselective rhodium(II)-catalyzed transannulation of aldehyde-tethered N-sulfonyl triazoles with electron-rich aromatic nucleophiles is reported for the first time to afford functionalized 6-substituted piperidin-3-ones. The reaction has a broad substrate scope including both aliphatic and aromatic N-sulfonyl-1,2,3-triazoles together with various aromatic nucleophiles. The addition of a catalytic amount of Lewis acid has proven to be crucial for the yield improvement. By employing this methodology, hardly accessible piperidin-3-ones bearing quaternary carbons could be obtained.
Synthesis of 5-Iodo-1,2,3,4-tetrahydropyridines by Rhodium-Catalyzed Tandem Nucleophilic Attacks Involving 1-Sulfonyl-1,2,3-triazoles and Iodides
Man, Zengming,Dai, Haican,Shi, Yinping,Yang, Dongdong,Li, Chuan-Ying
, p. 4962 - 4965 (2016/10/18)
Sodium iodide is used for the first time as a nucleophile to trap an α-imino rhodium carbene, which triggers a tandem process involving intermolecular nucleophilic attack and intramolecular SN2 reaction. A series of 5-iodo-1,2,3,4-tetrahydropyridines are obtained in high yield, and the synthetic utility of the products is demonstrated in cross-coupling reactions and the construction of biorelated polycyclic compounds.
Acid-catalyzed cyclization of vinylsilanes bearing a hydroxy group: A new method for stereoselective synthesis of disubstituted tetrahydrofurans
Miura,Okajima,Hondo,Nakagawa,Takahashi,Hosomi
, p. 11348 - 11357 (2007/10/03)
In the presence of a catalytic amount of TsOH or TiCl4, (Z)-5-silyl-4-penten-1-ols ((Z)-1) are smoothly cyclized to 2-silylmethyl-substituted tetrahydrofurans. This cyclization is applicable to the construction of a tetrahydropyran ring. The silyl group and the geometry of the C-C double bond strongly influence the cychzation rate. TBDMS and benzyldimethylsilyl groups considerably accelerate the cyclization in comparison with a dimethylphenylsilyl group, and (E)-vinylsilanes show much lower reactivity than the corresponding (Z)-isomers. The cyclization proceeds by stereospecific syn addition of the hydroxy group. Vinylsilanes 17, 19, and 21, (Z)-5-silyl-4-penten-1-ols bearing a substituent on the methylene tether, smoothly undergo the acid-catalyzed cyclization to give trans-2,5-, cis-2,4-, and trans-2,3-disubstituted tetrahydrofurans, respectively, with moderate to high stereoselectivity. The silyl group of some cychzed products can be easily converted into a hydroxy group with stereochemical retention.
Relative asymmetric induction in the intramolecular reaction between alkynes and cyclopropylcarbene-chromium complexes: Stereocontrolled synthesis of five-membered rings fused to oxygen heterocycles
Yan,Zhu,Matasi,Herndon
, p. 1291 - 1301 (2007/10/03)
Synthesis of cyclopentenone derivatives fused to oxygen heterocycles by means of the intramolecular coupling of alkynes and cyclopropylcarbene- chromium complexes has been examined for a variety of cases in which the tethering chain features a stereogenic
Design and Synthesis of Transition-state Analogues for a Cationic Cyclisation
Bell, Ian M.,Abell, Chris,Leeper, Finian J.
, p. 1997 - 2006 (2007/10/02)
Transition-state analogues based upon the 6-(hydroxymethyl)-13-azagona-1,3,5,(10),8-tetraene structure (e.g., 40) have been designed and synthesized as part of a programme to elicit antibodies capable of catalysing cationic cyclisations.Methodology for co
