Kinetic resolution of cis-3-alkylcyclohexene oxide by a chiral lithium amide - An application to a synthesis of both enantiomers of isomenthone

Heterocycles

Volumn 52, Issue 3, 2000, Pages 1029-1032

  Asami, Masatoshi ^a   Sato, Shinsuke ^a   Honda, Kiyoshi ^a   Inoue, Seiichi ^a  

^a YOKOHAMA NATIONAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; AMIDE; EPOXIDE; ISOMENTHONE; LITHIUM;

ARTICLE; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; GAS CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SYNTHESIS;

EID: 0034163418     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-99-S122     Document Type: Article

References (20)

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15. 1H-NMR, and MS spectra.
16. 20 was obtained by the catalytic hydrogenation of 3a.
17. J. A. Dale, D. L. Dull, and H. S. Mosher, J. Org. Chem., 1969, 34, 2543.
18. Epoxides (1b) and (1c) were prepared by a similar method as reported for 1a; G. Bellucci, G. Berti, M. Ferretti, G. Ingrosso, and E. Mastrorilli, J. Org. Chem., 1978, 43, 422.
19. 3 as a chiral shift reagent.
20. The absolute configuration was determined by the conversion of 1b to (-)-isomenthone.