Stereoselective synthesis of optically active 2-alkylpiperidines utilizing electrochemical oxidation as a key step

Author:

Onomura Osamu,Kanda Yasuhisa,Imai Mieko,Matsumura Yoshihiro

Publisher

Elsevier BV

Subject

Electrochemistry,General Chemical Engineering

Reference25 articles.

1. Asymmetric carbon-carbon bond-forming reaction at the 2-position of a piperidine skeleton

2. Copper ion-catalyzed asymmetric carbon–carbon bond-forming reaction at the 2-position of a piperidine skeleton

3. A new method for regioselective synthesis of 2-substituted 1-(methoxycarbonyl)-1,2-dihydropyridines

4. Electrochemical α-methoxylation of carbamates is applicable to a variety of 1-protected cyclic and acyclic amines (ref. [5]). The oxidation of 1-protected cyclic amines proceeds more smoothly (with less than 3F/mol) than that of acyclic carbamates (with more than 4F/mol), and N-alkoxycarbonyl group is the most suitable protecting group. For unsymmetrical carbamates, the oxidation takes place at the less substituted α-site. The reaction proceeds with two-electrons transfer from carbamates to anode. Although an alternative method for the preparation of 1-protected-2-methoxypyrrolidinone has been known (ref. [6]), the starting materials were different from those in electrochemical method, and the latter method is characterized by one-step procedure without using any oxidizing reagent.

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