- Direct oxidative carbon-carbon bond formation using the cation pool method. 1. Generation of iminium cation pools and their reaction with carbon nucleophiles
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We have developed a method that involves the generation of a cation pool using low-temperature electrolysis, and then its reaction with nucleophiles under non-oxidative conditions. This one-pot method solves problems associated with conventional oxidative generation of cations and their in situ reaction with nucleophiles, and provides an efficient method for direct oxidative carbon-carbon bond formation. As an example of this method, generation of cation pools from carbamates by low-temperature electrolysis (-72°C) and their reactions with carbon nucleophiles such as allylsilanes, enol silyl ethers, and enol acetates were examined and the desired products were obtained in good yields. Aromatic compounds and 1,3-dicarbonyl compounds can also be utilized as carbon nucleophiles. The present method was also applied to combinatorial parallel synthesis using a robotic synthesizer.
- Yoshida, Jun-ichi,Suga, Seiji,Suzuki, Shinkiti,Kinomura, Naoya,Yamamoto, Atsushi,Fujiwara, Kazuyuki
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- Mannich-type reaction of N,O-acetals with ketones mediated by a combination of TiCl4 and PhSiCl3
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A combination of TiCl4 and PhSiCl3 efficiently conducts the Mannich-type reaction of N,O-acetals with ketones to afford α-substituted cyclic amine derivatives in good yields. This method was applicable to preparation of azabicyclo co
- Kamogawa, Satoshi,Ikeda, Takashi,Kuriyama, Masami,Matsumura, Yoshihiro,Onomura, Osamu
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experimental part
p. 325 - 332
(2011/04/24)
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- Asymmetric introduction of nucleophiles to the 2-position of pyrrolidine ring through N-acylpyrrolidinium ion
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Asymmetric carbon-carbon bond-forming reaction at the 2-position of a pyrrolidine ring was achieved. The reaction involved a chiral Ti(IV) catalyzed coupling between 1-methoxycarboyl-2-methoxypyrrolidine and silyl enol ethers to afford 2-substituted pyrro
- Onomura, Osamu,Ikeda, Takashi,Matsumura, Yoshihiro
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- Anodic modification of proline derivatives using a lithium perchlorate/nitromethane electrolyte solution.
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[reaction: see text] N-Acyliminium cation of prolines was efficiently generated to accumulate in an undivided cell at 0 degrees C by an anodic oxidation of N-acylprolines or alpha'-phenylsulfanylated N-acylproline derivatives in a lithium perchlorate/nitr
- Kim, Shokaku,Hayashi, Kanako,Kitano, Yoshikazu,Tada, Masahiro,Chiba, Kazuhiro
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p. 3735 - 3737
(2007/10/03)
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- Electroorganic Chemistry. 46. A New Carbon-Carbon Bond Forming Reaction at the α-Position of Amines Utilizing Anodic Oxidation as a Key Step
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A new carbon-carbon bond forming reaction at the α-position of primary and secondary amines has been exploited.The method involves anodic oxidation of urethanes derived from the primary and secondary amines and subsequent acid-catalyzed reaction of the re
- Shono, Tatsuya,Matsumura, Yoshihiro,Tsubata, Kenji
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p. 1172 - 1176
(2007/10/02)
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