223690-77-5

Upstream product

• 1201013-85-5 C₁₅H₁₄⁽²⁾H₂O₃ 
• 1201013-83-3 C₁₅H₁₃⁽²⁾H₃O₃ 
• 1590-08-5 2-methyl-1-tetralone 
• 107-18-6 allyl alcohol 
• 20907-32-8 sodium allyloxide 
• 148624-14-0 3,4-dihydro-2-methyl-naphthalen-1-yl acetate 
• 1446139-94-1 C₁₄H₁₆O₂ 
• 40685-04-9 1,2,3,4-tetrahydro-2-(hydroxymethylene)naphthalen-1-one 
• 91962-77-5 2-methyl-1-oxo-1,2,3,4-tetrahydro-naphthalene-2-carbaldehyde 
• 76629-12-4 2-acetyl-2-methyl-3,4-dihydronaphthalen-1(2H)-one 
• 74477-40-0 trimethyl(2-methyl-3,4-dihydronaphthalen-1-yloxy)silane 
• 106-95-6 allyl bromide 

Downstream Products

• 240405-15-6 3-(1-hydroxy-2-methyl-1,2,3,4-tetrahydro-2-naphthalenyl)propyl benzoate 
• 240405-14-5 3-(1-hydroxy-2-methyl-1,2,3,4-tetrahydro-2-naphthalenyl)propyl benzoate 

Relevant academic research and scientific papers

The salt-free nickel-catalysed α-allylation reaction of ketones with allyl alcohol and diallylether

The nickel-catalysed α-allylation of ketones with allyl alcohol and diallylether has been performed under neutral conditions. As no base is involved, the products are synthesized without salts as side products. The dppf/Ni(cod)2 catalytic system in MeOH at 80 °C has been shown as the most effective reaction system to afford tetrasubstituted derivatives from various cyclic and acyclic ketones with one or two mobile protons. This process combined with a metathesis step yields spirocyclic compounds according to a salt free synthetic sequence.

Enol Acetates: Versatile Substrates for the Enantioselective Intermolecular Tsuji Allylation

A highly versatile enantioselective intermolecular Tsuji allylation that generates alpha-quaternary stereocenters is reported. The methodology utilizes a prochiral enol acetate as a substrate, which is the last class of the original Tsuji substrates to be

Development of asymmetric deacylative allylation

Herein we present the development of asymmetric deacylative allylation of ketone enolates. The reaction directly couples readily available ketone pronucleophiles with allylic alcohols using facile retro-Claisen cleavage to form reactive intermediates in situ. The simplicity and robustness of the reaction conditions is demonstrated by the preparation of >6 g of an allylated tetralone from commercially available materials. Furthermore, use of nonracemic PHOX ligands allows intermolecular formation of quaternary stereocenters directly from allylic alcohols.

Deacylative allylation: Allylic alkylation via retro-Claisen activation

A new method for allylic alkylation of a variety of relatively nonstabilized carbon nucleophiles is described herein. In this process of "deacylative allylation", the coupling partners, an allylic alcohol and a ketone pronucleophile, undergo in situ retro-Claisen activation to generate an allylic acetate and a carbanion. In the presence of palladium, these reactive intermediates undergo catalytic coupling to form a new C-C bond. In comparison to unimolecular decarboxylative allylation, a commonly utilized method for allylation of carbon anions, deacylative allylation is an intermolecular process. Moreover, deacylative allylation allows the direct coupling of readily available allylic alcohols. Lastly, the full utility of deacylative allylation is demonstrated by the rapid construction of a variety 1,6-heptadienes via 3-component couplings.

Palladium-catalyzed decarboxylative asymmetric allylic alkylation of enol carbonates

Palladium-catalyzed decarboxylative asymmetric allylic alkylation (DAAA) of allyl enol carbonates as a highly chemo-, regio-, and enantioselective process for the synthesis of ketones bearing either a quaternary or a tertiary R-stereogenic center has been investigated in detail. Chiral ligand L4 was found to be optimal in the DAAA of a broad scope of cyclic and acyclic ketones including simple aliphatic ketones with more than one enolizable proton. The allyl moiety of the carbonates has been extended to a variety of cyclic or acyclic disubstituted allyl groups. Our mechanistic studies reveal that, similar to the direct allylation of lithium enolates, the DAAA reaction proceeds through an "outer sphere" S N2 type of attack on the π-allylpalladium complex by the enolate. An important difference between the DAAA reaction and the direct allylation of lithium enolates is that in the DAAA reaction, the nucleophile and the electrophile were generated simultaneously. Since the π-allylpalladium cation must serve as the counterion for the enolate, the enolate probably exists as a tight-ion-pair. This largely prevents the common side reactions of enolates associated with the equilibrium between different enolates. The much milder reaction conditions as well as the much broader substrate scope also represent the advantages of the DAAA reaction over the direct allylation of preformed metal enolates.

Construction of chiral quaternary carbon centers by asymmetric alkylation of achiral lithium enolates mediated by chiral tetradentate ligands: Stoichiometric and catalytic approaches

Enantioselective asymmetric alkylation of achiral lithium enolates mediated by chiral tetradentate amine ligands is achieved to give chiral quaternary carbon centers. Turnover of a chiral tetradentate amine in the presence of an achiral bidentate amine during the reaction is also realized.