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Article

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Accepted version

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2014-11-25

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/169228

Substrate-controlled Michael additions of chiral ketones to enones

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https://doi.org/10.1021/ol503133j

Abstract

Substrate-controlled Michael additions of the titanium-(IV) enolate of lactate-derived ketone 1 to acyclic α,β-unsaturated ketones in the presence of a Lewis acid (TiCl4 or SnCl4) provide the corresponding 2,4-anti-4,5-anti dicarbonyl compounds in good yields and excellent diastereomeric ratios. Likely, the nucleophilic species involved in such additions are bimetallic enolates that may add to enones through cyclic transition states. Finally, further studies indicate that a structurally related β-benzyloxy chiral ketone can also participate in such stereocontrolled conjugate additions.

Subject

Àcids de Lewis, Titani, Cetones

Subject (English)

Lewis acids, Titanium, Ketones

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Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada)

Citation

FÀBREGAS, Mireia, et al. Substrate-controlled Michael additions of chiral ketones to enones. Organic Letters. 2014. Vol. 16, num. 23, pags. 6220-6223. ISSN 1523-7060. [consulted: 11 of August of 2026]. Available at: https://hdl.handle.net/2445/169228

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