Synthesis and microbial hydroxylation of some azabicycloalkanes

Olivo, Horacio F.; Hemenway, Michael S.; Gezginci, Mikail H.

doi:10.1016/s0040-4039(97)10876-0

Cited by 31 publications

(16 citation statements)

References 17 publications

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“…However, although 3a led to hydroxylated compound 4a in reasonable isolated yield, optical purity was far from being useful for synthetic purposes (Table 1, entry 1). [9] This result is in agreement with the literature because many other examples of moderate stereoselectivity have been reported [4,15] for the hydroxylating microorganism Beauveria bassiana. However, despite this general trend, a few highly selective biohydroxylations (80Ϫ90% optical purities) have also been observed [7,16,17] for this fungus.…”

Section: Introductionsupporting

confidence: 92%

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

Raadt¹,

Fetz²,

Griengl³

et al. 2000

Eur. J. Org. Chem.

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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

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Section: Introductionsupporting

confidence: 92%

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

Raadt¹,

Fetz²,

Griengl³

et al. 2000

Eur. J. Org. Chem.

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“…Equally challenging is selective functionalization of alcohols in the presence of amines. Designing a catalyst for this reaction requires either suppressing the innate superior nucleophilicity of the amino group (the "innate" reactivity in Scheme 41 a) [157] and/or enhancing the rate of the reaction with the alkoxy group. Two examples here elucidate these approaches.…”

Section: Catalytic Chemoselective Functionalization Of Heteroatomsmentioning

confidence: 99%

Catalytic Selective Synthesis

2012

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Complete control of the product of a catalytic reaction can be achieved on the basis of catalyst structure, even when the reaction conditions are nearly identical. Catalyst-controlled selectivity is well established for enantioselective catalysis but less formulated for catalytic regio-, chemo-, or product-selective reactions. This Review describes selective transformations of the same starting materials into two or more different products simply by the choice of catalyst. By collecting and highlighting examples of selective catalysis, we hope that the field will be encouraged by the progress that has been made while bringing attention to unmet needs in the design and mechanistic understanding of selective catalysts.

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“…¾hnlich schwierig stellt sich die selektive Funktionalisierung von Alkoholen in Anwesenheit vom Aminen dar. Ein Katalysator für eine derartige Umsetzung müsste entweder die intrinsische hçhere Nucleophilie der Amingruppe (siehe "intrinsische" Reaktivität in Schema 41 a) [157] unterdrücken und/oder eine Geschwindigkeitserhçhung der Reaktion am Alkohol erreichen. Zwei Beispiele sollen dies im Folgenden verdeutlichen.…”

Section: Angewandte Chemieunclassified

Katalytische selektive Synthese

2012

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Der Verlauf und das Produkt einer Reaktion lassen sich gezielt über die Katalysatorstruktur steuern, selbst bei nahezu identischen Reaktionsbedingungen. Katalysatorkontrollierte Selektivität ist in der enantioselektiven Synthese gut etabliert, in katalytischen regio‐, chemo‐ und produktselektiven Reaktionen aber wenig verbreitet. Dieser Aufsatz beschreibt, wie eine Ausgangsverbindung lediglich durch die Auswahl des Katalysators selektiv in zwei oder mehr unterschiedliche Produkte umgewandelt werden kann. Wir stellen Beispiele selektiver Katalysen vor und hoffen, dass die bisher erzielten Fortschritte ermutigend für das Gebiet sind. Zugleich wollen auch die noch offenen Fragen beim Entwurf und dem mechanistischen Verständnis selektiver Katalysatoren thematisieren.

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Synthesis and microbial hydroxylation of some azabicycloalkanes

Cited by 31 publications

References 17 publications

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

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

Catalytic Selective Synthesis

Katalytische selektive Synthese

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