Chiral Auxiliaries as Docking/Protecting Groups in Biohydroxylation: The Hydroxylation of Enantiopure Spirooxazolidines Derived from Cyclopentanone Using Beauveria bassiana ATCC 7159

✍ Scribed by Anna de Raadt; Barbara Fetz; Herfried Griengl; Markus Florian Klingler; Irene Kopper; Birgit Krenn; Dieter Franz Münzer; René Georg Ott; Peter Plachota; Hans Jörg Weber; Gerhard Braunegg; Winfried Mosler; Robert Saf

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 459 KB
• Volume: 2000
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/1099-0690(200012)2000:23<3835::aid-ejoc3835>3.0.co;2-e

✦ Synopsis

The aim of this work was to explore the scope and limitations of chiral docking/protecting groups as chiral auxiliaries in the biohydroxylation of unactivated methylene groups. As a model compound, cyclopentanone 1 was reacted with a range of enantiomerically pure amino alcohols 2a-n as well as 7a and b, varying substituents R 1 and R 2 . The resulting chiral spirooxazolidines 3a-n as well as 8a and b were exposed to the fungus Beauveria bassiana ATCC 7159 and the resultant hydroxylated products were characterised. Introducing chirality into the substrate before the fermentation was found to have a major effect on the course of the biohydroxylation relative to the achiral analogue 3a (Table 1, entry 1). The nature of R 1 /R 2 influenced both the product yield and [a] Spezialforschungsbereich F01 Biokatalyse,