0000000001145565

AUTHOR

Carolin Heescher

showing 3 related works from this author

1,2-Asymmetric Induction in Diastereo­selective Zwitterionic Aza-Claisen Rearrangements: Key Steps in Optically Active Alkaloid Synthesis

2013

The zwitterionic aza-Claisen rearrangement of optically active N-allylpyrrolidines and α-phenoxyacetyl fluorides proceeds with complete simple diastereoselectivity (internal asymmetric induction) and complete 1,2-asymmetric induction to generate a new C–C bond adjacent to a chiral C-N-Boc functionality. The resulting γ,δ-unsaturated amides were cyclised to give the corresponding pyrrolizidinones, which enabled the determination of the relative configuration of the stereotriads. Vinyl group degradation and a final lactam reduction gave an optically active analogue of (+)-petasinine (a pyrrolizidine alkaloid). Furthermore, the stereotriad-containing amides should be useful key intermediates f…

chemistry.chemical_compoundPyrrolizidine alkaloidChemistryStereochemistryOrganic ChemistryAlkaloid synthesisLactamTotal synthesisIndolizidinePhysical and Theoretical ChemistryOptically activeAsymmetric inductionEuropean Journal of Organic Chemistry
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CCDC 926977: Experimental Crystal Structure Determination

2013

Related Article: Carolin Heescher, Dieter Schollmeyer and Udo Nubbemeyer|2013|Eur.J.Org.Chem.|2013|4399|doi:10.1002/ejoc.201300389

Space GroupCrystallography2-Phenoxy-1-vinylhexahydro-3H-pyrrolizin-3-oneCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 926976: Experimental Crystal Structure Determination

2013

Related Article: Carolin Heescher, Dieter Schollmeyer and Udo Nubbemeyer|2013|Eur.J.Org.Chem.|2013|4399|doi:10.1002/ejoc.201300389

Space GroupCrystallography2-(2-Bromophenoxy)-1-vinylhexahydro-3H-pyrrolizin-3-oneCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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