58753-02-9

Upstream product

• 31053-10-8 4-iodocyclohexan-1-one 
• 98-88-4 benzoyl chloride 
• 1489-97-0 ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate 
• 5440-69-7 N-isopropylbenzamide 
• 96184-81-5 (+/-)-cyclohexanone-4-carboxaldehyde 
• 65-85-0 benzoic acid 
• 22460-52-2 4-bromocyclohexan-1-one 
• 93-97-0 benzoic acid anhydride 
• 142920-80-7 2-benzoyl-2-methoxycarbonylcyclohexanone 
• 142920-71-6 2-benzoyloxy-1-methoxycarbonylcyclohexene 
• 94020-44-7 C₁₆H₁₈O₂ 
• 94020-43-6 6-phenylbicyclo<3.2.1>oct-6-en-2-one 
• 142920-87-4 4-benzoyl-2-methoxycarbonylcyclohexanone 

Downstream Products

• 779358-26-8 [1-((R)-4-Methyl-cyclohex-3-enyl)-vinyl]-benzene 

Relevant academic research and scientific papers

Cobalt-Catalyzed Desymmetric Isomerization of Exocyclic Olefins

Chiral cyclic olefins, 1-methylcyclohexenes, are versatile building blocks for the synthesis of pharmaceuticals and natural products. Despite the prevalence of these structural motifs, the development of efficient synthetic methods remains an unmet challenge. Herein we report a novel desymmetric isomerization of exocyclic olefins using a series of newly designed chiral cobalt catalysts, which enables a straightforward construction of chiral 1-methylcyclohexenes with diversified functionalities. The synthetic utility of this methodology is highlighted by a concise and enantioselective synthesis of a natural product, β-bisabolene. The versatility of the reaction products is further demonstrated by multifarious derivatizations.

Enamines as Surrogates of Alkyl Carbanions for the Direct Conversion of Secondary Amides to α-Branched Ketones

A direct transformation of secondary amides into α-branched ketones with enamines as soft alkylation reagents was developed. In this reaction, enamines serve as surrogates of alkyl carbanions, rather than the conventional enolates equivalents in the Stork's reactions, which allowed for the easy introduction of alkyl groups with electrophilic functional groups. In the presence of 4 ? molecular sieves, the method can be extended to the one-pot coupling of secondary amides with aldehydes to yield ketones. (Figure presented.).

Gram-scale ketone synthesis by direct reductive coupling of alkyl iodides with acid chlorides

Alkyl aryl ketones were prepared on a gram scale by the nickel-catalyzed reductive coupling of alkyl iodides with aroyl chlorides. When scaled up 30-fold, this reaction shows a comparable coupling efficiency to the previously reported reaction performed under small-scale conditions. The mild and convenient reaction conditions show excellent tolerance to a range of functional groups and provide the ketones in good to excellent yields. Georg Thieme Verlag Stuttgart. New York.

Mild ketone formation via Ni-catalyzed reductive coupling of unactivated alkyl halides with acid anhydrides

Ni-catalyzed ketone formation through mild reductive coupling of a diverse set of unactivated alkyl bromides and iodides with particularly aryl acid anhydrides was successfully developed using zinc as the terminal reductant. These conditions also allow direct coupling of alkyl iodides with aryl acids in the presence of Boc2O and MgCl2. The Royal Society of Chemistry 2012.

Ketone formation via mild Nickel-catalyzed reductive coupling of alkyl halides with aryl acid chlorides

The present work highlights unprecedented Ni-catalyzed reductive coupling of unactivated alkyl iodides with aryl acid chlorides to efficiently generate alkyl aryl ketones under mild conditions.

Photochemical Reaction of 2-Acyloxy-1-methoxycarbonylcyclohexenes: an Efficient Aliphatic Photo-Fries Rearrangement and a Novel 1,5-Aroyl Migration

Upon irradiation 2-acyloxy-1-methoxycarbonylcyclohexenes readily undergo photo-Fries rearrangement to give 2-acyl-2-methoxycarbonylcyclohexanones in good yields and among them 2-aroyloxy-1-methoxycarbonylcyclohexenes also undergo a novel 1,5-aroyl migration according to irradiation conditions to give 4-aroyl-2-methoxycarbonylcyclohexanones, which result from 1,3-aroyl migration following photo-Fries rearrangement.