4096-34-8Relevant articles and documents
Havel,Chau
, p. 5800,5801, 5804 (1975)
Construction of bicyclic systems containing an oxygen bridge by isomerization of cyclic epoxy alcohols
Iwakura, Masaru,Tokura, Hiroshi,Tanino, Keiji
, p. 1223 - 1226 (2017)
A novel method for constructing a 7-oxabicyclo[2.2.1]heptane skeleton was developed. The substrates, namely cis-3,4-epoxy-1-cyclohexanol derivatives, were prepared from the corresponding 3-cyclohexen-1-ol derivatives via a stereoselective epoxidation reaction using a vanadium catalyst. Upon heating with lithium iodide in propionitrile, the cis-epoxy alcohol was transformed into the 7-oxabicyclo[2.2.1]heptane derivative in high yield. The reaction proceeds through formation of a lithium alkoxide bearing an iodohydrin moiety, followed by an intramolecular SN2 reaction.
Chiral Supramolecular U-Shaped Catalysts Induce the Multiselective Diels-Alder Reaction of Propargyl Aldehyde
Hatano, Manabu,Sakamoto, Tatsuhiro,Mizuno, Tomokazu,Goto, Yuta,Ishihara, Kazuaki
supporting information, p. 16253 - 16263 (2018/11/27)
The Diels-Alder reaction, which is a traditional [4 + 2] cycloaddition with two carbon-carbon bond formations, is one of the most powerful tools to synthesize versatile and unique six-membered rings. We show that chiral supramolecular U-shaped boron Lewis acid catalysts promote the unprecedented multiselective Diels-Alder reaction of propargyl aldehyde with cyclic dienes. Independent from the substrate control, enantio-, endo/exo-, π-facial-, regio-, site-, and substrate-selectivities could be controlled by the present U-shaped catalysts. The obtained reaction products could access the concise synthesis of chiral diene ligands and a key intermediate of (+)-sarkomycin. The results presented here might partially contribute to the development of artificial enzyme-like supramolecular catalysts for multiselective reactions, which will be able to target organic compounds that have thus far eluded synthesis.
Mn(III) complexes with tridentate N,N,O-ligands as catalysts for the epoxidation of alkenes
Aghmiz,Mostfa,Iksi,Rivas,Gonzalez,Diaz,El Guemmout,El Laghdach,Echarri,Masdeu-Bulto
, p. 2567 - 2577 (2013/08/23)
Mn(III) complexes with tridentate Schiff bases have been prepared and applied as catalyst precursors in epoxidation of alkenes using iodosobenzene as an oxidant providing high conversions and high selectivities when cyclohexene derivatives were studied.
