20047-19-2Relevant articles and documents
Stereoselective Synthesis of cis- And irans-2,3-Disubstituted Tetrahydrofurans via Oxonium-Prins Cyclization: Access to the Cordigol Ring System
Spivey, Alan C.,Laraia, Luca,Bayly, Andrew R.,Rzepa, Henry S.,White, Andrew J. P.
, p. 900 - 903 (2010)
Chemical Equation Presentation SnBr4-promoted oxonium-Prins cyclizations to form 2,3-disubstituted tetrahydrofurans (THFs) are reported. In the absence of an internal nucleophile, the carbocation intermediates are trapped by bromide to give 2,3
Lewis base activation of lewis acids: Development of a lewis base catalyzed selenolactonization
Denmark, Scott E.,Collins, William R.
, p. 3801 - 3804 (2007)
The concept of Lewis base activation of Lewis acids has been applied to the selenolactonization reaction. Through the use of substoichiometric amounts of Lewis bases with "soft" donor atoms (S, Se, P) significant rate enhancements over the background reac
Synthesis and Reactivity of Novel ?-Allylcyclopentadienyl Cobaltolactone Complexes
Christie, Steven D. R.,Cosset, Christophe,Hamilton, David R.,Kerr, William J.,O'Callaghan, John M.
, p. 2051 - 2052 (1995)
A range of novel cobaltolactone complexes are prepared under photolytic conditions from dicarbonylcyclopentadienylcobalt and vinyl epoxides; their subsequent reactivity under a selected series of reaction conditions is described.
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Servis,K.L.,Roberts,J.D.
, p. 1331 - 1339 (1965)
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Vanadium-catalyzed isomerization of cyclopropanemethanols to homoallylic alcohols involving C-C bond cleavage
Maeda, Yasunari,Nishimura, Takahiro,Uemura, Sakae
, p. 380 - 381 (2005)
Some vanadium compounds work as effective catalysts for isomerization of cyclopropanemethanols to the corresponding homoallylic alcohols. This reaction may proceed via [3,3]sigmatropic rearrangement involving an oxovanadium cyclopropanemethanolate accompa
Tandem five membered-ring selective Prins reaction and Friedel-Crafts reaction
Suzuki, Yuji,Niwa, Takanori,Yasui, Eiko,Mizukami, Megumi,Miyashita, Masaaki,Nagumo, Shinji
, p. 1337 - 1340 (2012)
A tandem reaction consisting of five membered-ring selective Prins cyclization and subsequent Friedel-Crafts cyclization was developed. The reactions of phenyl homoallylic alcohol 3 and benzaldehyde derivatives 6 afforded tetrahydroindenofurans 7 or penta
Radical C(sp3)-H Heck-type Reaction of N-Alkoxybenzimidoyl Chlorides with Styrenes to Construct Alkenols
Fang, Di,Zhang, Yidan,Chen, Yiyun
supporting information, p. 2050 - 2054 (2022/03/17)
We report the first radical C(sp3)-H Heck-type reaction of aliphatic alcohols for selective δ- and ?-alkenol synthesis by photoredox catalysis. N-Alkoxybenzimidoyl chlorides are developed as novel alkoxyl radical precursors with tunable redox potentials. Various alkenols can be constructed by the inert C(sp3)-H Heck-type reaction of 4-cyano-N-alkoxybenzimidoyl chlorides with styrene derivatives under redox-neutral conditions, which can be performed on the gram scale and can be easily derivatized.
Highly Regioselective 5-endo-tet Cyclization of 3,4-Epoxy Amines into 3-Hydroxypyrrolidines Catalyzed by La(OTf)3
Hoshino, Yoshihiko,Iwabuchi, Yoshiharu,Kuriyama, Yuse,Sasano, Yusuke,Uesugi, Shun-ichiro,Yamaichi, Aoto
supporting information, p. 1961 - 1965 (2021/01/04)
Highly regioselective intramolecular aminolysis of 3,4-epoxy amines has been achieved. Key features of this reaction are (1) chemoselective activation of epoxides in the presence of unprotected aliphatic amines in the same molecules by a La(OTf)3 catalyst and (2) excellent regioselectivity for anti-Baldwin 5-endo-tet cyclization. This reaction affords 3-hydroxy-2-alkylpyrrolidines stereospecifically in high yields. DFT calculations revealed that the regioselectivity might be attributed to distortion energies of epoxy amine substrates. The use of this reaction was demonstrated by the first enantioselective synthesis of an antispasmodic agent prifinium bromide.
