Chiral silicon groups as auxiliaries for enantioselective synthesis: Access to optically active silanes by biotransformation and the enantiospecific preparation of (R)-(+)-1-phenylethanol

Tetrahedron Asymmetry

Volumn 7, Issue 1, 1996, Pages 69-78

  Huber, Priska ^a   Bratovanov, Svetoslav ^a   Bienz, Stefan ^a   Syldatk, Christoph ^b   Pietzsch, Markus ^b  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b UNIVERSITY OF STUTTGART   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1 PHENYLETHANOL; SILANE DERIVATIVE;

ARTICLE; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; MICROORGANISM; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0030064125     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(95)00422-X     Document Type: Article

References (11)

1. Chapeaurouge, A.; Bienz, S., Helv. Chim. Acta 1993, 76, 1876.
2. Bienz, S.; Chapeaurouge, A., Helv. Chim. Acta 1991, 74, 1477.
3. Enev, V.; Stojanova, D.; Bienz, S., 'A Novel Stereoselective Reaction Cascade Leading from 1-Hydroxyallylsilanes to Aldol Type Products' and 'Silicon-Directed Stereoselective Preparation and Ester Enolate Rearrangement of α-Silylated O-Acylallylalcohols', manuscripts in preparation.
4. Fischer, L., Ph.D. thesis, Technische Universität Braunschweig, 1990.
5. Syldatk, C.; Andree, H.; Stoffregen, A.; Wagner, F.; Stumpf, B.; Ernst, L.; Zilch, H.; Tacke, R., Appl. Microbiol. Biotechnol. 1987, 27, 152.
6. Syldatk, C.; Stoffregen, A.; Wuttke, F.; Tacke, R., Biotechnol. Letters 1988, 10, 731.
7. The specific activity was calculated with respect to the bio dry mass, not to an enzyme concentration. The conversion factor 'immobilized cells/bio dry mass' is composed of the load of matrix (12.5% bio wet mass) and the ratio of 'bio wet mass/bio dry mass' of 4.16.
8. Dale, J. A.; Mosher, H. S., J. Am. Chem. Soc. 1973, 95, 512.
9. Bratovanov, S.; Linden, A.; Bienz, S., Acta Crystallogr., Sect. C 1995, submitted for publication.
10. 4 to the compounds (+)-4/(-)-5 and (+)-5/(-)-4, respectively, and these four alcohols were converted to the Mosher derivatives. The NMR spectra of these products exhibited the same enantiomeric excesses as were determined for the original alcohols (+)-4 and (+)-5.
11. Brook, A. G.; Jones, P. F., J. Chem. Soc., Chem. Commun. 1969, 1324.