Deracemization of (±)-2,2-disubstituted epoxides via enantioconvergent chemoenzymatic hydrolysis using nocardia EH1 epoxide hydrolase and sulfuric acid

Tetrahedron Letters

Volumn 38, Issue 10, 1997, Pages 1753-1754

  Orru, Romano V A ^a   Kroutil, Wolfgang ^a   Faber, Kurt ^a  

^a GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; EPOXIDE HYDROLASE; SULFURIC ACID;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; HYDROLYSIS; NOCARDIA; STEREOISOMERISM;

EID: 0031562470     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00201-3     Document Type: Article

References (11)

1. 1. a) For a review see: Faber, K.; Mischitz, M.; Kroutil, W. Acta Chem. Scand. 1996, 50, 249.
2. b) Pedragosa-Moreau, S.; Archelas, A.; Furstoss, R. Tetrahedron 1996, 52, 4593.
3. c) Osprian, I.; Kroutil, W.; Mischitz, M.; Faber, K. Tetrahedron: Asymmetry 1997, 8, 1.
4. 2. For a review on 'second-generation biotransformations' see: Stecher, H.; Faber, K. Synthesis 1997, in press.
5. 3. Archer, I. V. J.; Leak, D. J.; Widdowson, D. A. Tetrahedron Lett. 1996, 37, 8819.
6. 4. Mischitz, M.; Mirtl, C.; Saf, R., Faber, K. Tetrahedron: Asymmetry 1996, 7, 2041.
7. 2-mechanism: Biggs, J.; Chapman, N. B.; Finch, A. F.; Wray, V. J. Chem. Soc. (B) 1971, 55.
8. 6. Mischitz, M.; Kroutil, W.; Wandel, U.; Faber, K. Tetrahedron: Asymmetry 1995, 6, 1261.
9. 4, no diols were formed and elimination and/or rearrangement was the major reaction.
10. 3), diols (S)-1a-3a were extracted with EtOAc (5 × 10 mL) and analyzed as described in ref. 1c.
11. 9. I.e. slightly beyond 50%, see: Vänttinen, E.; Kanerva, L. T. Tetrahedron: Asymmetry 1995, 6, 1779.