First example of memory of chirality in carbenium ion chemistry

Organic Letters

Volumn 2, Issue 12, 2000, Pages 1689-1691

  Matsumura, Yoshihiro ^a   Shirakawa, Yuki ^a   Satoh, Yuki ^a   Umino, Meri ^a   Tanaka, Takayoshi ^a   Maki, Toshihide ^a   Onomura, Osamu ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001374592     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005795t     Document Type: Article

References (18)

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12. Compound 6 was prepared from L-serine, see; Garner P.; Park, J. M. J. Org. Chem. 1987, 52, 2361-2364.
13. G347 graphite plate (Tokai Carbon Co., Ltd.) was used as an anode.
14. Electro-generated acids can be formed in the vicinity of an anode; Baizer, M. M. In Organic Electrochemistry; Lund, H., Baizer, M. M., Eds.; Marcel Dekker: New York, 1991; Chapter 30.
15. The starting material 6 was mainly recovered.
16. Silica gel, AcOEt/hexane = 1/5.
17. Treatment of (4R,5R)-9 with 5% formic acid in methanol (at -20 °C for 90 h) gave a mixture of (4R,5R)-9 and (4S,5R)-10 in a ratio of 55/ 45.
18. The difference between graphite and Pt in the electrochemical oxidation of organic compounds has been reported previously. Ross, S. D.; Finkelstein, M. J. Org. Chem. 1969, 34, 2923-2927.