An article CuH-Catalyzed Enantioselective Ketone Allylation with 1,3-Dienes: Scope, Mechanism, and Applications WOS:000462950800034 published article about ASYMMETRIC-SYNTHESIS; CARBONYL-COMPOUNDS; (S)-2-CYCLOHEXYL-2-PHENYLGLYCOLIC ACID; TRANSFER HYDROGENATION; OXYPHENONIUM BROMIDE; TERTIARY ALCOHOLS; BOND FORMATION; RUTHENIUM; HYDROHYDROXYALKYLATION; DIENES in [Li, Chengxi; Liu, Richard Y.; Yang, Yang; Buchwald, Stephen L.] MIT, Dept Chem, Cambridge, MA 02139 USA; [Jesikiewicz, Luke T.; Liu, Peng] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA in 2019.0, Cited 82.0. Product Details of 99-93-4. The Name is 4′-Hydroxyacetophenone. Through research, I have a further understanding and discovery of 99-93-4
Chiral tertiary alcohols are important building blocks for the synthesis of pharmaceutical agents and biologically active natural products. The addition of carbon nucleophiles to ketones is the most common approach to tertiary alcohol synthesis but traditionally relies on stoichiometric organometallic reagents that are difficult to prepare, sensitive, and uneconomical. We describe a mild and efficient method for the copper-catalyzed allylation of ketones using widely available 1,3-dienes as allylmetal surrogates. Homoallylic alcohols bearing a wide range of functional groups are obtained in high yield and with good regio-, diastereo-, and enantioselectivity. Mechanistic investigations using density functional theory (DFT) implicate the in situ formation of a rapidly equilibrating mixture of isomeric copper(I) allyl complexes, from which the Curtin-Hammett kinetics determine major isomer of the product. A stereochemical model is provided to explain the high diastereo-enantioselectivity of this process. Finally, this method was applied to the preparation of an important drug, (R)-procyclidine, and a key intermediate in the synthesis of several pharmaceuticals.
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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
,Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles