Preparation of S-(-)-2-acetoxymethyl-2,5-dihydrofuran and S-(-)-N-Boc- 2-hydroxymethyl-2,5-dihydropyrrole by enzymatic resolution

Tetrahedron Asymmetry

Volumn 9, Issue 3, 1998, Pages 403-406

  Schieweck, Frank ^a   Altenbach, Hans Josef ^a  

^a UNIVERSITY OF WUPPERTAL   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 ACETOXYMETHYL 2,5 DIHYDROFURAN; 2 HYDROXYMETHYL 2,5 DIHYDROPYRROLE; FURAN DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; ENZYME MECHANISM; ESTERIFICATION; HYDROLYSIS; NONHUMAN; OPTICAL ROTATION; PRIORITY JOURNAL; PSEUDOMONAS FLUORESCENS;

EID: 0032512604     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00008-1     Document Type: Article

References (18)

1. 1. Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis, VCH, Weinheim; 1995. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry, Pergamon, Oxford, 1994.
2. 1. Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis, VCH, Weinheim; 1995. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry, Pergamon, Oxford, 1994.
3. 2. Altenbach, H.-J.; Merhof, G. F.; Brauer, D. J. Tetrahedron: Asymmetry 1996, 7, 2493.
4. 3. Furan-2-carboxylic acid: Divanfard, H. R.; Joullié, M. M. Org. Prep. Proc. Int. 1978, 10, 94; Masamune, T.; Matsue, H.; Murase, H. Bull. Chem. Soc. Jpn. 1979, 52, 127.
5. 3. Furan-2-carboxylic acid: Divanfard, H. R.; Joullié, M. M. Org. Prep. Proc. Int. 1978, 10, 94; Masamune, T.; Matsue, H.; Murase, H. Bull. Chem. Soc. Jpn. 1979, 52, 127.
6. 4. Pyrrole-2-carboxylic acid: Donohoe, T. J.; Guyo, P. M. J. Org. Chem. 1996, 61, 7664.
7. 5. Weissfloch, A. N. E.; Kazlauskas, R. J. J. Org. Chem. 1995, 60, 6959.
8. 6. Screening with enzymes from: Candida antarctica B (Novozym 435), Candida cylindracea (Sigma), Candida cylindracea (Meito MY), Pseudomonas cepacia (Amano PS), Pseudomonas fluorescens (Fluka), Aspergillus oryzae (Lipozym IM), Pseudomonas species (Amano AK), Alcaligens species (Meito PL), Acromobacter species (Meito AL), pig pancreas lipase (type II, Aldrich) and pig liver esterase.
9. 7. General procedure for screening: 0.25 mmol substrate and 5 mg enzyme in 1.7 mL solvent.
10. 8. Chen, C.-S.; Fujimori, Y.; Girdauskas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294.
11. 9. Acylation with vinyl butyrate did not improve the specificity significantly.
12. 10. Further experiments at +6°C and -3°C resulted in lower enantioselectivities.
13. 11. Cleophax, J.; Hildesheim, J.; Gero, S. D. Bull. Soc. Chim. France 1967, 4111.
14. 12. Correa, A.; Dennis, J.-N.; Greene, A. E. Synth. Commun. 1991, 21, 1.
15. 13. For examples see: Holland, D.; Stoddart, J. F. J. Chem. Soc., Perkin Trans. 1 1983, 1553; Huwe, C. M.; Blechert, S. Synthesis 1997, 61; Baldwin, J. E.; Field, R. A.; Lawrence, C. C.; Lee, V.; Robinson, J. K.; Schofield, C. J. Tetrahedron Lett. 1994, 35, 4649 and references cited therein; Altenbach, H.-J.; Brauer, D. J.; Merhof, G. F. Tetrahedron 1997, 53, 6019.
16. 13. For examples see: Holland, D.; Stoddart, J. F. J. Chem. Soc., Perkin Trans. 1 1983, 1553; Huwe, C. M.; Blechert, S. Synthesis 1997, 61; Baldwin, J. E.; Field, R. A.; Lawrence, C. C.; Lee, V.; Robinson, J. K.; Schofield, C. J. Tetrahedron Lett. 1994, 35, 4649 and references cited therein; Altenbach, H.-J.; Brauer, D. J.; Merhof, G. F. Tetrahedron 1997, 53, 6019.
17. 13. For examples see: Holland, D.; Stoddart, J. F. J. Chem. Soc., Perkin Trans. 1 1983, 1553; Huwe, C. M.; Blechert, S. Synthesis 1997, 61; Baldwin, J. E.; Field, R. A.; Lawrence, C. C.; Lee, V.; Robinson, J. K.; Schofield, C. J. Tetrahedron Lett. 1994, 35, 4649 and references cited therein; Altenbach, H.-J.; Brauer, D. J.; Merhof, G. F. Tetrahedron 1997, 53, 6019.
18. 13. For examples see: Holland, D.; Stoddart, J. F. J. Chem. Soc., Perkin Trans. 1 1983, 1553; Huwe, C. M.; Blechert, S. Synthesis 1997, 61; Baldwin, J. E.; Field, R. A.; Lawrence, C. C.; Lee, V.; Robinson, J. K.; Schofield, C. J. Tetrahedron Lett. 1994, 35, 4649 and references cited therein; Altenbach, H.-J.; Brauer, D. J.; Merhof, G. F. Tetrahedron 1997, 53, 6019.