- A New Method for Introducing Some Active Methylene or Methine Groups to the 3-Position of Pyrrolidine or Piperidine Skeleton, and Its Application to Preparation of a Key Intermydiate for (+/-)-Eburnamonine Synthesis
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A new method for introducing a bis(methoxycarbonyl)methyl or 2-oxopropyl group to the 3-position of pyrrolidine or piperidine skeleton has been exploited, and this method could be used in the synthesis of a key intermediate for the (+/-)-eburnamonine synthesis.
- Shono, Tatsuya,Matsumura, Yoshihiro,Ogaki, Masaru,Onomura, Osamu
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Read Online
- Characterization of Cyclic N-Acyliminium Ions by Infrared Ion Spectroscopy
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N-Acyliminium ions are highly reactive intermediates that are important for creating CC-bonds adjacent to nitrogen atoms. Here we report the characterization of cyclic N-acyliminium ions in the gas phase, generated by collision induced dissociation tandem mass spectrometry followed by infrared ion spectroscopy using the FELIX infrared free electron laser. Comparison of DFT calculated spectra with the experimentally observed IR spectra provided valuable insights in the conformations of the N-acyliminium ions.
- Merx, Jona,Houthuijs, Kas J.,Elferink, Hidde,Witlox, Eva,Mecinovi?, Jasmin,Oomens, Jos,Martens, Jonathan,Boltje, Thomas J.,Rutjes, Floris P. J. T.
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supporting information
(2022/01/06)
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- Diastereoselective synthesis of 3-fluoro-2-substituted piperidines and pyrrolidines
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A facile procedure for synthesis of trans-3-fluoro-2-substituted piperidines by utilizing electrophilic fluorination of cyclic enamines and Lewis acid mediated nucleophilic substitution has been developed. Also, optically active trans-2-allyl-3-fluorinate
- Gichuhi, Paul N.,Kuriyama, Masami,Onomura, Osamu
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p. 331 - 346
(2014/01/17)
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- A new and efficient synthesis of derivatives of octahydro-4H-pyrrolo[1,2-c] pyrido[1′,2′-a]imidazole
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When diethyl malonate was added to a solution of Δ1- piperideine, generated in situ by oxidative desamination and decarboxylation of L-lysine by N-bromosuccinimide (NBS), formation of the unexpected tricyclic compound 6 (4-diethylmalonyl-octahydro-4H-pyrrolo[1,2-c]pyrido[1′, 2′-a]imidazole)was observed. The structure of 6 was deduced from analysis of its spectroscopic data and was confirmed both by chemical degradation and by total synthesis. We proved that 3-bromo-1-piperideine was implicated in its formation. Moreover, based on this feature, a new and efficient synthesis of 6 was developed. The elaborated pathway was adapted to access derivatives related to 6 that differed in their C-4 substituent. A new and efficient synthesis of derivatives of the tricyclic heterocycle A from lysine is described. A mechanism involving 3-halopiperideines as intermediates and based on a ring contraction followed by Michael reaction is proposed and tested. Copyright
- Rouchaud, Anne,Braekman, Jean-Claude
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experimental part
p. 2346 - 2353
(2011/06/22)
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- Stereoselective synthesis of 3-deoxy-piperidine iminosugars from l-lysine
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A new method using electrochemical oxidation and/or OsO4 oxidation has been used for the stereoselective synthesis of 2,3,6-trihydroxylated (5S)-piperidine derivatives. The electrochemical method was successively used for the conversion of N-pr
- Moriyama, Noriaki,Matsumura, Yoshihiro,Kuriyama, Masami,Onomura, Osamu
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scheme or table
p. 2677 - 2687
(2010/04/29)
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- Stereoselective synthesis of azasugars by electrochemical oxidation
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A new method using electrochemical oxidation has been exploited for the stereoselective synthesis of 2,3,6-trihydroxylated 5S-piperidine derivatives. The electrochemical method was successively used for the conversion of N-protected piperidines to N-prote
- Furukubo, Shigeru,Moriyama, Noriaki,Onomura, Osamu,Matsumura, Yoshihiro
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p. 8177 - 8181
(2007/10/03)
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- A convenient method for synthesis of optically active methylphenidate from N-methoxycarbonylpiperidine by utilizing electrochemical oxidation and Evans aldol-type reaction
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A new method to prepare optically active methylphenidate starting from piperidine is described. The method consists of a transformation of N-methoxycarbonylated piperidine to the corresponding α-methoxylated carbamate utilizing electrochemical oxidation f
- Matsumura, Yoshihiro,Kanda, Yasuhisa,Shirai, Kimihiro,Onomura, Osamu,Maki, Toshihide
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p. 7411 - 7422
(2007/10/03)
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- Reactivity of 2-Cyano-1,4,5,6-tetrahydro-1-pyridinecarboxylic Acid Esters Towards Various Nucleophiles: Regio- and Stereoselectivity of the Attack
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The synthesis and reactivity of the title compounds towards nucleophiles are discussed. The regio- and diastereoselectivity of the attack is highly dependent on the carbamic ester and the type of nucleophile applied. Both Michael type addition across the
- Stanetty,Mihovilovic,Mereiter
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p. 1061 - 1072
(2007/10/03)
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- REGIOSELECTIVE INTRODUCTION OF ALKYL GROUPS TO THE POSITION α OR γ TO NITROGEN ATOM OF PIPERIDINE SKELETONS USING ANODIC OXIDATION IN A KEY STEP
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β,γ-Unsaturated N-alkoxycarbonyl-α-methoxypiperidines, which were prepared from N-alkoxypiperidines by using anodic oxidation in a key step, were regioselectively alkylated at the α-position by using Grignard reagents in the presence of BF3*Et2O, whereas in the presence of CuBr, the alkylation took place at the γ-position.
- Shono, Tatsuya,Terauchi, Jun,Ohki, Yoshihisa,Matsumura, Yoshihiro
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p. 6385 - 6386
(2007/10/02)
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- A NEW METHOD FOR REGIOSELECTIVE SYNTHESIS OF 2-SUBSTITUTED 1-(METHOXYCARBONYL)-1,2-DIHYDROPYRIDINES
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2-Substituted 1,2-dihydropyridines including an optically active one were regioselctively prepared from 2-substituted piperidines through three intermediates, that is, (a) 1,2,3,4-tetrahydropyridines, (b) 5-bromo-6-methoxypiperidines, and (c) 1,2,3,4-tetrahydro-6-methoxypyridines.
- Shono, Tatsuya,Matsumura, Yoshihiro,Onomura, Osamu,Yamada, Yasufu
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p. 4073 - 4074
(2007/10/02)
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- A NEW METHOD OF ACYLATION AT β-POSITION OF ALIPHATIC AMINES
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A new method to introduce an acyl or a formyl group to β-position of aliphatic amines was studied using encarbamates, prepared from α-methoxycarbamates, as key intermediates.
- Shono, Tatsuya,Matsumura, Yoshihiro,Tsubata, Kenji,Sugihara, Yoshihiro
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p. 1201 - 1204
(2007/10/02)
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- Electroorganic Chemistry. 60. Electroorganic Synthesis of Enamides and Enecarbamates and Their Utilization in Organic Synthesis.
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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.
- Shono, Tatsuya,Matsumura, Yoshihiro,Tsubata, Kenji,Sugihara, Yoshihiro,Yamane, Shin-ichiro,et. al.
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p. 6697 - 6703
(2007/10/02)
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