Scalable Synthesis of Enantiomerically Pure Bicyclo[2.2.2]octadiene Ligands

An operationally simple and scalable synthesis of enantiomerically pure bicyclo[2.2.2]octadiene (bod*) ligands relying on an organocatalytic one-pot Michael addition–aldol reaction with cheap 2-cyclohexenone and phenylacetaldehyde is presented. The crystalline bicyclic product 4a (6-hydroxy-5-phenyl...

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Veröffentlicht in:	Journal of organic chemistry 2012-05, Vol.77 (10), p.4765-4773
Hauptverfasser:	Abele, Stefan, Inauen, Roman, Spielvogel, Dirk, Moessner, Christian
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetaldehyde - analogs & derivatives Acetaldehyde - chemistry Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Bridged Bicyclo Compounds - chemical synthesis Bridged Bicyclo Compounds - chemistry Catalysis Catalysts: preparations and properties Chemistry Cyclohexanones - chemistry Exact sciences and technology General and physical chemistry Ligands Molecular Structure Organic chemistry Preparations and properties Stereoisomerism Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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