2019
DOI: 10.1002/ejoc.201901043
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Synthesis of α,ω‐Bis‐Enones by the Double Addition of Alkenyl Grignard Reagents to Diacid Weinreb Amides

Abstract: An efficient double addition of substituted alkenylmagnesium bromides to bis‐Weinreb amides has been developed, giving α,ω‐bis‐enones that are building blocks for certain drugs and polymers. Furthermore, reliable protocols for the preparation of the required substituted alkenylmagnesium reagents from substituted non‐activated alkenyl bromides are reported. The double addition is demonstrated on 25 examples, including enantiopure as well as conjugated and cross‐conjugated bis‐enones. The addition to a cyclohexa… Show more

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Cited by 3 publications
(4 citation statements)
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“…Using general procedure F, from 8h (0.10 mmol), diketone 9h was obtained in 18% yield (21 mg): 1 H NMR (500 MHz, CDCl 3 ) δ 7.63 (d, J = 16.3 Hz, 2H), 7.60–7.53 (m, 4H), 7.42–7.38 (m, 6H), 6.80 (d, J = 16.3 Hz, 2H), 3.10 (s, 4H). The spectrum matches previously reported data …”
Section: Methodssupporting
confidence: 91%
See 1 more Smart Citation
“…Using general procedure F, from 8h (0.10 mmol), diketone 9h was obtained in 18% yield (21 mg): 1 H NMR (500 MHz, CDCl 3 ) δ 7.63 (d, J = 16.3 Hz, 2H), 7.60–7.53 (m, 4H), 7.42–7.38 (m, 6H), 6.80 (d, J = 16.3 Hz, 2H), 3.10 (s, 4H). The spectrum matches previously reported data …”
Section: Methodssupporting
confidence: 91%
“…The spectrum matches previously reported data. 53 (2RS,3RS)-2,3-Dimethyl-1,4-diphenylbutane-1,4-dione (9i). Products were purified by silica gel chromatography eluting with 40% ethyl acetate in hexane, giving a white solid.…”
Section: ■ Conclusionmentioning
confidence: 99%
“…The majority of reports feature the enone functionality as a suitable Michael acceptor which has been shown to reverse at elevated temperatures and/or under basic conditions. However, synthetic enone species typically suffer with poor stability and require low atom economy, multistep syntheses to fabricate . Use of l -carvone as a bio-sourced building block for photopolymer resins not only offers a cost-effective solution, but also shifts reliance from traditionally used oil derivatives to a more sustainable source.…”
Section: Introductionmentioning
confidence: 99%
“…However, synthetic enone species typically suffer with poor stability and require low atom economy, multistep syntheses to fabricate. 17 Use of L-carvone as a bio-sourced building block for photopolymer resins not only offers a cost-effective solution, 18 but also shifts reliance from traditionally used oil derivatives to a more sustainable source.…”
Section: ■ Introductionmentioning
confidence: 99%