Enzyme-catalyzed synthesis and absolute configuration of (1S,2R,5S)- and (1R,2S,5R)-2-(1-hydroxyethyl)-1-(methoxymethyloxyethyl)cyclobutane-1- carbonitrile, key intermediates for the preparation of chiral cyclobutane- containing pheromones

Tetrahedron Asymmetry

Volumn 11, Issue 8, 2000, Pages 1691-1695

  Petschen, I ^a   Bosch, M P ^a   Guerrero, A ^a  

^a CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYANIDE; CYCLOBUTANE DERIVATIVE; PHEROMONE;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOMER; ENZYME MECHANISM; NONHUMAN; PRIORITY JOURNAL; SYNTHESIS;

EID: 0034607931     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00101-4     Document Type: Article

References (21)

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2. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: New York, 1990.
3. Bisacchi, G. S.; Braitman, A.; Cianti, C. W.; Clark, J. M.; Field, A. K.; Hagan, M. E.; Hockstein, D. R.; Malley, M. F.; Mitt, T.; Slusarchyk, W. A.; Sundeen, J. E.; Terry, B. J.; Toumari, A. V.; Weaver, E. R.; Young, M. G.; Zahler, R. J. Med. Chem. 1991, 34, 1415.
4. Bloor, S. J. Tetrahedron Lett. 1993, 34, 5617.
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8. (c) Boyer, F.-D.; Ducrot, P.-H. Eur. J. Org. Chem. 1999, 1201.
9. Stork, G.; Cohen, J. F. J. Am. Chem. Soc. 1974, 96, 5270.
10. Rossini, G.; Marotta, E.; Raimondi, A.; Righi, P. Tetrahedron: Asymmetry 1991, 2, 123 and references cited therein.
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14. For reviews, see: (a) Chen, C. S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695.
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17. 3) for an e.e. ≥99%.
18. 3) (e.e. ≥99%).
19. 19F NMR signals of the Mosher esters were the following: (R)-MTPA of (1S,2R,5S)-3: δ -71.38; (S)-MTPA of (1S,2R,5S)-3: δ -71.63; (R)-MTPA of (1R,2S,5R)-3: δ -71.63; (S)-MTPA of (1R,2S,5R)-3: δ -71.38 ppm.
20. Harvey, I.; Crout, D. H. G. V. Tetrahedron: Asymmetry 1993, 4, 807.
21. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.