Enantioselective Microbial Reduction of 5-Acetylisoxazolines - A Novel Method for Stereochemical Control on Yeast Reduction

The kinetics and the stereoselectivity of the reduction by baker′s yeast of racemic 5‐acetyl‐4,5‐dihydro‐3‐phenylisoxazole 1 to the corresponding alcohol in 2‐propanol/water mixtures are strongly dependent from the 2‐propanol/water ratio; at a ratio of 4.0, the reduction allows a kinetic resolution...

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Veröffentlicht in:	Liebigs Annalen der Chemie 1989-12, Vol.1989 (12), p.1257-1259
Hauptverfasser:	Ticozzi, Calimero, Zanarotti, Antonio
Format:	Artikel
Sprache:	eng
Schlagworte:	4,5‐Dihydroisoxazole 5-Dihydroisoxazole Applied microbiology Aspergillus niger Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Fundamental and applied biological sciences. Psychology Methods. Procedures. Technologies Microbiology Miscellaneous Yeast
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Beschreibung
Zusammenfassung:	The kinetics and the stereoselectivity of the reduction by baker′s yeast of racemic 5‐acetyl‐4,5‐dihydro‐3‐phenylisoxazole 1 to the corresponding alcohol in 2‐propanol/water mixtures are strongly dependent from the 2‐propanol/water ratio; at a ratio of 4.0, the reduction allows a kinetic resolution leading to alcohol 2 and ketone (R)‐1 Subsequent reduction of (R)‐1 with yeast in water and with Aspergillus niger leads to alcohols 3 and 4 with high ee.
ISSN:	0170-2041 1099-0690
DOI:	10.1002/jlac.198919890299