Resolution of both enantiomers of 5-chloro-5-methyl-2-cyclopentenone

Journal of Organic Chemistry

Volumn 67, Issue 22, 2002, Pages 7902-7903

  McMorris, Trevor C ^a   Staake, Michael D ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOMERS;

CATALYSIS; OXIDATION;

ORGANIC COMPOUNDS;

5 CHLORO 5 METHYL 2 CYCLOPENTENONE; CYCLOPENTENONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0036827840     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026030x     Document Type: Article

References (8)

1. McMorris, T. C.; Yu, J.; Lira, R.; Dawe, R.; MacDonald, J. R.; Waters, S. J.; Estes, L. A.; Kelner, M. J. J. Org. Chem. 2001, 66, 6158.
2. Rizzo, C. J.; Dujlap, N. K.; Smith, A. B., III J. Org. Chem. 1987, 52, 5280.
3. Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551.
4. Kurosu, M. K.; Kishi, Y. J. Org. Chem. 1998, 63, 6100.
5. Although the yield of alcohols was 61%, no starting ketone was recovered. Thus it is unlikely that any enantiomeric enrichment due to kinetic resolution took place under these conditions. At low temperature (-40° C), the reduction rate was slower and differed for the two ketones.
6. 3, which gave a mixture of cis and trans alcohols. The diastereomers were separated and each enatiomeric pair was converted to its (R)-MTPA esters. NMR analysis showed that the trans alcohols gave a 1:1 mixture of (R)-MTPA esters. Likewise the cis alcohols gave a 1:1 mixture. Thus no enrichment due to kinetic resolution took place and the ee values are valid.
7. Limanto, J.; Snapper, M. L. J. Am. Chem. Soc. 2000, 122, 8071.
8. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.