Facile synthesis of substituted phenanthroline ligands by samarium-promoted coupling of phenanthroline with ketones

Organic Letters

Volumn 1, Issue 10, 1999, Pages 1659-1662

  O'Neill, David J ^a   Helquist, Paul ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; LIGAND; PHENANTHROLINE DERIVATIVE; SAMARIUM;

ARTICLE; CHEMISTRY; SYNTHESIS;

KETONES; LIGANDS; PHENANTHROLINES; SAMARIUM;

EID: 0033581787     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990284w     Document Type: Article

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72. In this initial survey of the reactivity of various types of ketones, the stereochemistry of the products from addition to chiral ketones has not been rigorously established. Only single stereoisomers of the products 1f and 1g from the reactions of (-)-thujone and DL-menthone were detected in the crude reaction mixtures. For the (-)-thujone-derived series of products, a NOESY NMR study of the methoxy derivative 3f provided the cross-correlations shown below in support of the assigned stereochemistry.