Regio- and stereoselective nucleophilic addition reactions of Swaminathan ketone and its methylated analog using organometallic reagents

[Display omitted] Herein, we report the regio- and stereoselective nucleophilic addition reactions of Swaminathan ketone 2a and its methylated analog 2b, both of which contain a 6–7 fused carbocyclic enedione moiety. Nucleophilic additions to 2 using generic organometallic reagents, such as Grignard...

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Veröffentlicht in:Tetrahedron letters 2023-11, Vol.132, p.154800, Article 154800
Hauptverfasser: Ohno, Shun, Ito, Mina, Aoki, Shiho, Inomata, Kohei
Format: Artikel
Sprache:eng
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Zusammenfassung:[Display omitted] Herein, we report the regio- and stereoselective nucleophilic addition reactions of Swaminathan ketone 2a and its methylated analog 2b, both of which contain a 6–7 fused carbocyclic enedione moiety. Nucleophilic additions to 2 using generic organometallic reagents, such as Grignard and organolithium reagents, preferentially occurs at the conjugated carbonyl group to afford a range of tert-alcohols with high stereoselectivity. The selectivity observed with 2 was notable when compared to that observed with Wieland–Miescher ketone 1a bearing a decalin framework. A variety of substituents, such as alkyl, alkenyl, alkynyl and aryl groups, can be introduced into 2 using this method. Exceptionally, the allylation reaction of 2 occurred at both the conjugated and non-conjugated carbonyl groups, but this regioselectivity problem was solved using organocopper reagents.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2023.154800