33707-37-8Relevant academic research and scientific papers
An efficient synthesis of chiral isoquinuclidines by Diels - Alder reaction using Lewis acid catalyst
Hirama, Masafumi,Kato, Yuji,Seki, Chigusa,Nakano, Hiroto,Takeshita, Mitsuhiro,Oshikiri, Noriko,Iyoda, Masahiko,Matsuyama, Haruo
experimental part, p. 7618 - 7624 (2011/02/22)
The Diels-Alder reaction of 1,2-dihydropyridine derivatives (1-phenoxycarbonyl-1,2-dihydropyridine 1 or 1-methoxycarbonyl-1,2- dihydropyridine 4) with N-acryloyl (1S)-2,10-camphorsultam (1S)-2 {or N-acryloyl (1R)-2,10-camphorsultam (1R)-2} in the presence of Lewis acid, such as titanium tetrachloride, zirconium tetrachloride, and hafnium tetrachloride afforded the endo-cycloaddition product, 2-azabicyclo[2.2.2]octane derivatives in good yields with excellent diastereoselectivity. The absolute stereochemistry assignment of the endo-cycloaddition product (1S)-5a starting from N-acryloyl (1S)-2,10-camphorsultam (1S)-2 has been established to be (1S,4R,7S) and the reaction mechanism was proposed.
Thermal and induced decompositions of N′-alkoxycarbonyldihydropyridines: End product analysis and EPR spectra of azacyclohexadienyl radicals
Baguley, Paul A.,Walton, John C.
, p. 1423 - 1429 (2007/10/03)
Hydrogen abstraction from N-alkoxycarbonyldihydropyridines generated azacyclohexadienyl radicals (pyridinyl radicals) which are characterised by EPR spectroscopy. In the presence of peroxide initiators, N-alkoxycarbonyl-1,2-dihydropyridines decomposed with production of pyridine, the corresponding alkyl formate, alkyl benzoate and alkanol being formed as the major products. Absence of cyclised products in experiments with substrates containing hex-5-enyl, pent-4-enyloxy etc. units demonstrates that radical production must be minor and that N-alkoxycarbonylazacyclohexadienyl radicals do not readily undergo ss-scission of the exocyclic N-C bond. The most probable mechanism is a direct 1,2-elimination of formate. The alcohols which accompanied the other products are probably formed by hydrolysis of the formates and benzoates. Analogous chemistry is displayed by N-alkoxycarbonyl-1,4-dihydropyridines at higher temperatures where 1,4-elimination of formate is too rapid for homolytic radical production to compete.
Electroorganic Chemistry. 60. Electroorganic Synthesis of Enamides and Enecarbamates and Their Utilization in Organic Synthesis.
Shono, Tatsuya,Matsumura, Yoshihiro,Tsubata, Kenji,Sugihara, Yoshihiro,Yamane, Shin-ichiro,et. al.
, p. 6697 - 6703 (2007/10/02)
A variety of enecarbamates and enamides were synthesized from α-methoxy carbamates and α-methoxy amides prepared by anodic methoxylation of amine derivatives.Some new carbon-carbon bond-forming reactions and hydroxylation at the β position of amines have been accomplished by using these enecarbamates and enamides as key intermediates.Also, new synthetic routes of nicotinaldehyde and pyrrole derivatives have been exploited by utilizing anodic dimethoxylation of carbamates of piperidine and pyrrolidine, respectively.
