Unprecedented chemo-enzymatic synthesis of stereochemically pure 3-acetoxy-2-methyl-2-vinylcycloalkanones

Tetrahedron Letters

Volumn 45, Issue 8, 2004, Pages 1763-1767

  Fuhshuku, Ken Ichi ^a   Tomita, Mina ^a   Sugai, Takeshi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

Hydroxyketone; Radical fragmentation; Substituted cyclohexanone; Substituted cyclopentanone

Indexed keywords

3 ACETOXY 2 METHYL 2 VINYLCYCLOHEXANONE; 3 ACETOXY 2 METHYL 2 VINYLCYCLOPENTANONE; ALKANONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; FRAGMENTATION REACTION; REDUCTION; STEREOCHEMISTRY;

EID: 0842326655     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.084     Document Type: Article

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24. 4, and concentrated in vacuo. The residue was purified by silica gel column chromatography.
25. R=26.8 and 27.6 min], the β-fragmentation product 7e of microbial origin coincided the peak of 26.8 min, and its ee was determined to be >99.9%. As, no racemization was observed in this β-fragmentation process, the absolute configuration of 7e was unambiguously confirmed to be (2S,3S).
26. R=15.4 and 15.8 min], the β-fragmentation product 8e of microbial origin coincided the peak of 15.4 min, and its ee was determined to be >99.9%.
27. 4: C, 64.98; H, 8.39.
28. 4: C, 59.39; H, 8.97.
29. 2: C, 62.12; H, 10.95.
30. 3: C, 78.07; H, 7.74.