Stereoselective syntheses of piperidinones and their modification by organometallic coupling reactions |
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Authors: | Kranke Birgit Kunz Horst |
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Affiliation: | Institut für Organische Chemie, Johannes Gutenberg-Universit?t Mainz, Duesbergweg 10-14, 55128, Mainz, Germany. |
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Abstract: | Dehydropiperidinones stereoselectively obtained from N-arabinosyl imines were iodinated at the enaminone structure. Knochel iodine-magnesium exchange afforded Grignard compounds of these piperidinone derivatives which reacted, either directly or after transmetalation to zinc or copper intermediates, with alkyl-, aryl- or acylhalides to give correspondingly substituted piperidinones. Stereoselective conjugate allyl cuprate addition to a thus obtained 5-allyl dehydropiperidinone and ring-closing metathesis of the product gave a hydroquinolinone containing three stereogenic centers. |
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