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Volumn 50, Issue 25-26 SPEC. ISS., 2005, Pages 4926-4935

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

Author keywords

2 Methoxy 3,4 didehydropiperidines; Catalytic asymmetric reaction; Copper ion catalyzed; Electrochemical oxidation; Optically active 2 alkylpiperidines

Indexed keywords

CARBON; CATALYSTS; CHEMICAL BONDS; COPPER; IONS; OXIDATION; SYNTHESIS (CHEMICAL);

EID: 24344465813     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.electacta.2005.01.053     Document Type: Conference Paper
Times cited : (11)

References (25)
  • 4
    • 24344469319 scopus 로고    scopus 로고
    • note
    • 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 3 F/mol) than that of acyclic carbamates (with more than 4 F/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.
  • 7
    • 0030605144 scopus 로고    scopus 로고
    • An alternative method preparation of 1-protected-2-methoxypyrrolidine; reduction of 1-protected 2-pyrrolidinone with DIBAL; M. Pichon, B. Figadere, and A. Cave Tetrahedron Lett. 37 1996 7963
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7963
    • Pichon, M.1    Figadere, B.2    Cave, A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.