Stereocontrolled Access to Enantiopure 7‑Substituted cis- and trans-Octahydroindoles

Cyclocondensation of (R)-phenylglycinol with stereoisomeric mixtures (racemates, cis/trans) of 3-substituted 2-oxocyclo­hexane­acetates stereoselectively afforded tricyclic oxazoloindolone lactams, from which straightforward procedures for the stereocontrolled formation of enantiopure 7-substituted...

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Bibliographic Details
Published in:Organic letters 2016-11, Vol.18 (22), p.5836-5839
Main Authors: Ghirardi, Elena, Griera, Rosa, Piccichè, Miriam, Molins, Elies, Fernández, Israel, Bosch, Joan, Amat, Mercedes
Format: Article
Language:English
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Summary:Cyclocondensation of (R)-phenylglycinol with stereoisomeric mixtures (racemates, cis/trans) of 3-substituted 2-oxocyclo­hexane­acetates stereoselectively afforded tricyclic oxazoloindolone lactams, from which straightforward procedures for the stereocontrolled formation of enantiopure 7-substituted octahydro­indoles with a variety of stereochemical patterns have been developed. The methodology has been successfully applied to the synthesis of (+)-α-lycorane.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b02861