Dynamic kinetic resolution in the microbial reduction of α-monosubstituted β-oxoesters: The reduction of 2-carbethoxy-cycloheptanone and 2-carbethoxy-cyclooctanone

Tetrahedron Asymmetry

Volumn 8, Issue 11, 1997, Pages 1735-1739

  Danchet, Sylvie ^a   Bigot, Carine ^a   Buisson, Didier ^a   Azerad, Robert ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANONE;

ARTICLE; DRUG SYNTHESIS; MOLECULAR DYNAMICS; PRIORITY JOURNAL; REDUCTION; STEREOISOMERISM; STEREOSPECIFICITY; YEAST;

EID: 0031006995     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00171-7     Document Type: Article

References (43)

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38. Flexibond™ OV-1701 capillary column (Pierce Chem. Co, 15 m × 0.25 mm), 135°C, ret. times: 3, 7.08 min; 5, 8.41 min; 4, 12.4 min; 6, 13.7 min.
39. OV1701 capillary column, 135°C (10 min) then 135-170°C (2°C/min), ret. times: 3, 32.6 min; ent-3, 32.9 min; ent-5, 34.0 min; 5, 34.4 min. BP20 capillary column (SGE, 25 m × 0.25 mm), 160°C (20 min) then 160-190°C (4°C/min): ent-4, 51.2 min; 4, 51.8 min; ent-6, 54.4 min; 6, 55.2 min.
40. H1H2=7 Hz.
41. Enantiomers of cis-and trans-hydroxyesters 3 and 5 have been occasionally reported in the literature (Xie, Z.-F; Nakamura, I.; Suemune, H.; Sakai, K. J. Chem. Soc., Chem. Commun. 1988, 966, cited in Kitamura, M.; Ohkuma, T.; Tokunaga, M.; Noyori, R. Tetrahedron: Asymmetry 1990, 1, 1), but without any optical rotation measurement, and without clear and justified stereochemical assignments. However, the levorotatory optical rotations attributed to the 1R-isomers in the referred paper are in agreement with our results.
42. Enantiomers of cis-and trans-hydroxyesters 3 and 5 have been occasionally reported in the literature (Xie, Z.-F; Nakamura, I.; Suemune, H.; Sakai, K. J. Chem. Soc., Chem. Commun. 1988, 966, cited in Kitamura, M.; Ohkuma, T.; Tokunaga, M.; Noyori, R. Tetrahedron: Asymmetry 1990, 1, 1), but without any optical rotation measurement, and without clear and justified stereochemical assignments. However, the levorotatory optical rotations attributed to the 1R-isomers in the referred paper are in agreement with our results.
43. Meyers, A. I.; Williams, D. R.; Erickson, G. W.; White, S.; Druelinger, M. J. Am. Chem. Soc. 1981, 103, 3081.