Stereoselective synthesis of isoflavonoids. (R)- and (S)-isoflavens

α-Benzylation of (+)- and (−)-N-phenylacetyl imidazolidinones with 2-O-methoxy-methylbezyl bromides, followed by reductive removal of the chiral auxiliary and cyclization, afforded oxygenated isoflavans in excellent enantiomeric excess and yield. α-Benzylated (+)- and (−)-N-phenylacetyl imidazolidin...

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Bibliographic Details
Published in:Tetrahedron 1999-03, Vol.55 (11), p.3365-3376
Main Authors: Versteeg, Marietjie, Bezuidenhoudt, Barend C.B., Ferreira, Daneel
Format: Article
Language:English
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Summary:α-Benzylation of (+)- and (−)-N-phenylacetyl imidazolidinones with 2-O-methoxy-methylbezyl bromides, followed by reductive removal of the chiral auxiliary and cyclization, afforded oxygenated isoflavans in excellent enantiomeric excess and yield. α-Benzylated (+)- and (−)-N-phenylacetyl imidazolidinones serve as percursors to isoflavans in excellent enantiomeric excess following reductive deamination and cyclization of the intermediate 2,3-diaryl-propan-1-ols. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(98)01147-8