Stereoselective construction of cyclic ethers using a tandem two-component etherification: Elucidation of the role of bismuth tribromide
The stereodivergent construction of cyclic ethers remains an important area of synthetic interest, particularly given the ubiquity of C-glycoside derivatives in natural and unnatural pharmacologically important agents. This work describes a series of intr
Evans, P. Andrew,Cui, Jian,Gharpure, Santosh J.,Hinkle, Robert J.
On the choice of Lewis acids for the Prins reaction; two total syntheses of (±)-Civet
While developing new variations of the Prins cyclisation reaction, the effect of the choice of Lewis acid on the outcome of the reaction and the product(s) has been investigated, yielding hitherto unseen dihydropyran products in the Prins cyclisation reac
Chio, Freda K.,Warne, Julie,Gough, Damien,Penny, Mark,Green, Sasa,Coles, Simon J.,Hursthouse, Mike B.,Jones, Peter,Hassall, Lorraine,McGuire, Thomas M.,Dobbs, Adrian P.
supporting information; experimental part
p. 5107 - 5124
(2011/07/31)
Multicatalytic synthesis of complex tetrahydrofurans involving bismuth(iii) triflate catalyzed intramolecular hydroalkoxylation of unactivated olefins
A multicatalytic synthesis of complex tetrahydrofurans has been developed involving a Bi(OTf)3-catalyzed nucleophilic addition/ hydroalkoxylation sequence. Complex tetrahydrofuranyl products may be formed rapidly in high yield and with good diastereoselectivity. The demonstrated scope of hydroalkoxylation has also been expanded to include substrates bearing useful functional handles including carboxylate ester, olefin, nitrile, and nitro groups.
Kelly, Brendan D.,Allen, Julia M.,Tundel, Rachel E.,Lambert, Tristan H.
supporting information; experimental part
p. 1381 - 1383
(2009/10/02)
Platinum-catalyzed intramolecular hydroalkoxylation of γ- and δ-hydroxy olefins to form cyclic ethers
Reaction of 2,2-diphenyl-4-penten-1-ol with a catalytic mixture of [PtCl2(H2C=CH2)]2 (1 mol %) and P(4-C6H4CF3)3 (2 mol %) at 70 °C for 24 h led to the isolation of 2-
Qian, Hua,Han, Xiaoqing,Widenhoefer, Ross A.
p. 9536 - 9537
(2007/10/03)
Stereoselective Construction of cis-2,6-Disubstituted Tetrahydropyrans via the Reductive Etherification of δ-Trialkylsilyloxy Substituted Ketones: Total Synthesis of (-)-Centrolobine
(Matrix presented). The stereoselective intramolecular reductive etherification of δ-trialkylsilyloxy substituted ketones with catalytic bismuth tribromide and trielhylsilane provides a convenient method for the construction of cis-2,6-disubstituted tetra
Evans, P. Andrew,Cui, Jian,Gharpure, Santosh J.
p. 3883 - 3885
(2007/10/03)
Titanium-Mediated Carbonyl Olefinations. 2. Benzylidenations of Carbonyl Compounds with Dibenzyltitanocene
Mild thermolysis of carbonyl compounds with dibenzyltitanocene affords phenyl-substituted olefins, enol ethers, and enamines.
Petasis, Nicos A.,Bzowej, Eugene I.
p. 1327 - 1330
(2007/10/02)
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