A "designer yeast" that catalyzes the kinetic resolutions of 2-alkyl-substituted cyclohexanones by enantioselective Baeyer-Villiger oxidations

Journal of Organic Chemistry

Volumn 61, Issue 22, 1996, Pages 7652-7653

  Stewart, Jon D ^a   Reed, Kieth W ^a   Zhu, Jun ^b   Chen, Gang ^b   Kayser, Margaret M ^b  

^a University of Florida ^*  (United States)

^b UNIVERSITY OF NEW BRUNSWICK   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000779198     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961028p     Document Type: Article

References (25)

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16. Alphand, V.; Archelas, A.; Furstoss, R. J. Org. Chem. 1990, 55, 347-350. For a more exhaustive compilation of references describing the application of cyclohexanone monooxygenase to organic synthesis, see ref 14 and references therein.
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18. Ketones that were not commercially available were prepared by alkylation of the morpholine enamine of cyclohexanone: Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell J. Am. Chem. Soc. 1963, 85, 207-221. While many ketones could be successfully oxidized by our "designer yeast", this reagent was unable to oxidize either 2-benzyl- or 2-isobutylcyclohexanone since these hydrophobic compounds prevented growth of the cells, even in the presence of cyclodextrins.
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21. 4), filtered, and evaporated. The residue was chromatographed over silica gel using 1:1 ether:hexanes as the eluant to afford 29 mg of the (S)-ketone (58% yield) and 44 mg of the (R)-lactone (78% yield).
22. (a) Bar, R. Trends Biotechnol. 1989, 7, 2-4.
23. (b) In general, 1 equiv of β-cyclodextrin was sufficient to solubilize the ketones in the aqueous growth medium; however, the biotransformation of 2-isopropylcyclohexanone required 2.0 equiv of hydroxypropyl-β-cyclodextrin to afford a homogeneous mixture.
24. Note that the (R/S) designation is reversed for 1d, 2d, 1f, and 2f as a result of a change in priority numbers for the substituents.
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