Pd(0)-Catalyzed Conjugate Addition of Benzylzinc Chlorides to α,β-Enones in an Atmosphere of Carbon Monoxide: Preparation of 1,4-Diketones
- 13 January 2004
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (3) , 908-914
- https://doi.org/10.1021/jo035468+
Abstract
Pd(0)-catalyzed conjugate addition of benzylzinc chloride to methyl vinyl ketone in the presence of chlorotrimethylsilane and lithium chloride in an atmosphere of carbon monoxide at room temperature afforded 1-phenyl-2,5-hexanedione monosilyl enol ether. In this catalytic carbonylation, four components are connected in one reaction. Successive acidic workup generated a variety of 1,4-diketones from substituted benzylzinc chlorides or related compounds and alpha,beta-enones. Some products were converted to cyclopentenones or five-membered heterocyclic compounds containing an N, O, or S atom.Keywords
This publication has 45 references indexed in Scilit:
- Four carbon component coupling reaction based on free-radical carbonylation: an easy access to .beta.-functionalized .delta.,.epsilon.-unsaturated ketonesJournal of the American Chemical Society, 1993
- Palladium(0)‐Catalyzed Three‐Component Coupling Reaction of Allyl Benzoates, Carbon Monoxide, and ZincioestersAngewandte Chemie International Edition in English, 1992
- (Z)-7-Nitro-3-Heptene as Central Intermediate for the Synthesis of Jasmone, Methyl Jasmonate, and γ JasmolactoneSynthetic Communications, 1989
- Simple one-step synthesis of 1,4-diketones: a new approach to dihydrojasmoneThe Journal of Organic Chemistry, 1988
- Synthesis of some thiophenium bis(t-butoxycarbonyl)methylidesJournal of the Chemical Society, Perkin Transactions 1, 1988
- An Efficient Synthetic Method of Jasmone Analogues and 2,5-Dialkylpyrrolidine Alkaloids Using 1-Benzyl-2,5-dicyanopyrrolidineChemistry Letters, 1987
- Oxocyclopentenol synthesesThe Journal of Organic Chemistry, 1985
- Direct nucleophilic 1,4-acylation of .alpha.,.beta.-unsaturated ketones and aldehydes via acylcuprate reagentsJournal of the American Chemical Society, 1985
- Utilization of trimethylsilylpropyne as an acetonyl unit in the synthesis of cyclopentenones. Applications to the synthesis of jasmone and dihydrojasmoneCanadian Journal of Chemistry, 1978
- Addition von Aldehyden an aktivierte Doppelbindungen, XI. Addition aliphatischer, heterocyclischer und aromatischer Aldehyde an ButenonEuropean Journal of Inorganic Chemistry, 1976