153816-17-2Relevant academic research and scientific papers
Base-induced rearrangement of dihydropyran oxides: A novel synthesis of cyclic enol ethers with a hydroxy-function in the allylic-position
Schmidt, Bernd
, p. 4319 - 4320 (1999)
A sequence of ring closing metathesis of allyl-homoallyl ethers, epoxidation of the resulting dihydropyrans, and rearrangements of the dihydropyran oxides with LDA provides convenient access to 2,3-dihydropyrans with a hydroxy group in the 4-position. The
Synthesis of Nitrogen- And Oxygen-Containing Heterocycles by Prins Cyclization in Continuous Flow
Talavera-Alemán, Armando,Marrot, Jérome,Dagousset, Guillaume,Thomassigny, Christine
, p. 1478 - 1488 (2020/12/22)
Aza-silyl-Prins and oxa-Prins cyclization reactions in continuous-flow chemistry are described for the synthesis of the corresponding tetrahydropyridines and pyran derivatives, respectively. In particular, the use of pyridine-carboxaldehydes for aza-silyl-Prins reaction led to either a symmetrical triarylmethane or two new bicyclic compounds. 4-Fluorinated-2-substituted tetrahydropyran derivatives were also obtained in the oxa-Prins cyclization with good selectivity in favor of the anti -isomer.
Ruthenium-catalyzed tandem olefin metathesis-oxidations
Scholte, Andrew A.,Mi, Hyun An,Snapper, Marc L.
, p. 4759 - 4762 (2007/10/03)
(Chemical Equation Presented) The utility of Grubbs' 2nd generation metathesis catalyst has been expanded by the development of two tandem olefin metathesis/oxidation protocols. These ruthenium-catalyzed processes provide cis-diols or α-hydroxy ketones from simple olefinic starting materials.
Epoxide opening reactions of aryl substituted dihydropyran oxides: Regio- And stereochemical studies directed towards deoxy-aryl-Cglycosides
Schmidt, Bernd
, p. 2627 - 2637 (2007/10/03)
2-Aryl-substituted tetrahydropyrans with 3,4- or 4,5-/ra;w-configured oxo substituents have been synthesized via ring-closing metathesis of allyl homoallyl ethers, epoxidation of the resulting dihydropyrans and opening of the epoxides with O-nucleophiles
Anodic Cyclization of Unsaturated α-Stannyl Ethers. Termination by Bromide derived from Dibromomethane
Yoshida, Jun-ichi,Takada, Kazunori,Ishichi, Yuji,Isoe, Sachihiko
, p. 2361 - 2362 (2007/10/02)
Anodic oxidation of unsaturated α-stannyl ethers in Bu4NClO4-CH2Br2 results in effective cyclization and the introduction of bromide into one of the original olefinic carbons; a mechanism involving the coupling between the cyclized carbocation and Br- generated by cathodic reduction of CH2Br2 is suggested.
