New synthetic method of optically active α-methylproline and α-methylpipecolinic acid using electrochemical oxidation as a key reaction

Tetrahedron Letters

Volumn 37, Issue 46, 1996, Pages 8395-8398

  Matsumura, Yoshihiro ^a   Kinoshita, Toshio ^a   Yanagihara, Yuka ^a   Kanemoto, Noriko ^a   Watanabe, Mitsuaki ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; PIPERIDINE DERIVATIVE; PROLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ELECTROCHEMISTRY; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030580351     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01919-3     Document Type: Article

References (17)

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4. b) Seebach, D.; Naef, R. Helv. Chim. Acta 1981, 64, 2704-2708.
5. c) Seebach, D.; Boes, M.; Naef, R.; Schweitzer, W. B. J. Am. Chem. Soc. 1983, 105, 5390-5398.
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8. 3. Shono, T.; Matsumura, Y.; Tsubata, K. Org. Synth. 1985, 63, 206-213.
9. 25 +69.3°(c 0.76 MeOH).
10. 4.
11. RT+73.1° (c 1.7 MeOH)]
12. 7. Beck, A.K.; Blank, S.; Job, K.; Seebach, D.; Sommerfeld, T. Org. Synth. 1993, 72, 62-73.
13. 8. Shono, T.; Matsumura, Y.; Tsubata, K.; Uchida, K. J. Org. Chem. 1986, 51, 2590-2592.
14. 9. It also could not be determined by NMR spectra if 2b′ was a mixture of stereoisomers or not.
15. 1H NMR spectrum of the amide prepared from 5b and Mosher's acid chloride showed that the obtained 5b had 84%ee.
16. 11. Seebach, D.; Dziadulewicz, R.; Behrendt, L.; Cantreggi, S.; Fitzi, R. Liebigs Ann.Chem. 1989, 1215-1232.
17. 25-4.9° (c 1.05 MeOH).