55666-45-0

Upstream product

• 2051-95-8 succinylbenzene 
• 115-11-7 isobutene 
• 1663-39-4 tert-Butyl acrylate 
• 100-52-7 benzaldehyde 
• 36952-37-1 (E)-N-(3-methylpyridin-2-yl)-1-phenylmethanimine 
• 75-65-0 tert-butyl alcohol 
• 98946-18-0 tert-Butyl 2,2,2-trichloroacetimidate 
• 611-73-4 Benzoylformic acid 
• 32864-38-3 tert-Butyl ethyl malonate 
• 70-11-1 α-bromoacetophenone 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 15026-17-2 succinic acid mono-tert-butyl ester 

Downstream Products

• 1006728-95-5 (S)-tert-butyl 4-hydroxy-4-phenylbutanoate 
• 5279-78-7 (1R*,2R*)-tert-butyl 2-phenylcyclopropanecarboxylate 
• 5279-78-7 t-butyl (1S,2S)-trans-2-phenyl-cyclopropane-1-carboxylate 
• 1357377-77-5 tert-butyl 4-(4-methoxyphenylimino)-4-phenylbutanoate 

Relevant academic research and scientific papers

Nickel-Mediated Photoreductive Cross Coupling of Carboxylic Acid Derivatives for Ketone Synthesis**

A simple visible light photochemical, nickel-catalyzed synthesis of ketones from carboxylic acid-derived precursors is presented. Hantzsch ester (HE) functions as a cheap, green and strong photoreductant to facilitate radical generation and also engages in the Ni-catalytic cycle to restore the reactive species. With this dual role, HE allows for the coupling of a large variety of radicals (1°,2°, benzylic, α-oxy & α-amino) with aroyl and alkanoyl moieties, a new feature in reactions of this type. With both precursors deriving from abundant carboxylic acids, this protocol is a welcome addition to the organic chemistry toolbox. The reaction proceeds under mild conditions without the need for toxic metal reagents or bases and shows a wide scope, including pharmaceuticals and complex molecular architectures.

Direct Synthesis of Chiral NH Lactams via Ru-Catalyzed Asymmetric Reductive Amination/Cyclization Cascade of Keto Acids/Esters

Lactams with a stereogenic center adjacent to the N atom have existed in many medicinal agents and bioactive alkaloids. Herein we report a broadly applicable synthesis of enantioenriched NH lactams through a one-pot asymmetric reductive amination/cyclization sequence of easily available keto acids/esters. Such cascade processes alleviate the demand for protecting group manipulations as well as intermediate purification. This strategy is capable of constructing enantioenriched lactams and benzo-lactams of a five-, six-, or seven-membered ring in generally high yield and with excellent enantioselectivities (up to 97% ee). Scalable and concise syntheses of key drug intermediates have further displayed the importance of this methodology.

Acyl radicals from α-keto acids using a carbonyl photocatalyst: Photoredox-catalyzed synthesis of ketones

Acyl radicals have been generated from α-keto acids using inexpensive and commercially available 2-chloro-thioxanthen-9-one as the photoredox catalyst under visible light illumination. These reactive species added to olefins or coupled with aryl halides via a bipyridylstabilized Ni(II) catalyst, enabling easy access to a diverse range of ketones. This reliable, atom-economical, and eco-friendly protocol is compatible with a wide range of functional groups.

Catalytic Redox Chain Ring Opening of Lactones with Quinones to Synthesize Quinone-Containing Carboxylic Acids

Catalytic ring opening of five- to eight-membered lactones with quinones is achieved through a redox chain mechanism. With low loading of a simple metal triflate Lewis acid catalyst and a chain initiator, C-H bonds of many quinones were efficiently functionalized with carboxylic acid-containing side chains. This method also features 100% atom economy and wide substrate scope. A novel route to the anti-asthma drug Seratrodast was developed. Mechanism study suggests that the redox chain reaction likely undergoes a carbocation intermediate.

Copper-Catalyzed Oxidative Cleavage of Electron-Rich Olefins in Water at Room Temperature

A copper-catalyzed oxidative cleavage of electron-rich olefins into their corresponding carbonyl derivatives is described as an alternative to ozonolysis. The scope includes various precursors to aryl ketone derivatives, as well as oxidations of enol ethers bearing atypical alkyl and dialkyl substitution, the first of their kind among such metal catalyzed alkene cleavage reactions. The use of an inexpensive copper salt, room temperature conditions, an aerobic atmosphere, and water as the global reaction medium highlight the green features of this new method. Associated mechanistic investigations are also presented.

Guiding a divergent reaction by photochemical control: Bichromatic selective access to levulinates and butenolides

Allylic and acrylic substrates may be efficiently transformed by a sequential bichromatic photochemical process into derivatives of levulinates or butenolides with high selectivity when phenanthrene is used as a regulator. Thus, UV-A photoinduced cross-metathesis (CM) couples the acrylic and allylic counterparts and subsequent UV-C irradiation initiates E-Z isomerization of the carbon-carbon double bond, followed by one of two competing processes; namely, cyclization by transesterification or a 1,5-H shift and tautomerization. Quantum chemical calculations demonstrate that intermediates are strongly blue-shifted for the cyclization while red-shifted for the 1,5-H shift reaction. Hence, delaying the double bond migration by employing UV-C absorbing phenanthrene, results in a selective novel divergent all-photochemical pathway for the synthesis of fundamental structural motifs of ubiquitous natural products.

Visible-Light-Promoted Synthesis of 1,4-Dicarbonyl Compounds via Conjugate Addition of Aroyl Chlorides

A facile visible-light photocatalytic conjugate addition to prepare 1,4-dicarbonyl compounds has been developed by employing readily available aroyl chlorides as aryl radical sources. This operationally simple method shows a broad scope with regard to both aroyl chlorides and Michael acceptors. As a result, a variety of 1,4-diketones were efficiently synthesized in moderate to good yields.

Copper-Catalyzed Synthesis of γ-Amino Acids Featuring Quaternary Stereocenters

The first general asymmetric synthesis of γ,γ-disubstituted γ-amino acids by copper-catalyzed ring opening of nonstrained lactones with amines is reported. This approach features ample scope, operational simplicity, and wide functional-group diversity. The catalytic process allows access to a series of highly functionalized enantioenriched γ-amino acids featuring quaternary stereocenters with excellent enantiomeric ratios of up to 98:2 and excellent yields of up to 98 %.

Photoredox-Catalyzed Hydroacylation of Olefins Employing Carboxylic Acids and Hydrosilanes

A hydroacylation reaction of alkenes has been achieved employing readily available carboxylic acids as the acyl source and hydrosilanes as a hydrogen source via photoredox catalysis. The combination of both single electron transfer and hydrogen atom transfer steps has dramatically expanded new applications of carboxylic acids in organic synthesis. The protocol also features extremely mild conditions, broad substrate scope, and good functional group tolerance, affording a novel and convenient approach to hydroacylation of alkenes.

Organocatalytic route to enantioselective synthesis of ceramide trafficking inhibitor HPA-12

A new organocatalytic approach to the synthesis of ceramide trafficking inhibitor HPA-12 has been described starting from phenacyl bromide. The strategy involves chiral CBS reduction of γ-ketoester and proline-catalyzed α-amination reaction of aldehyde fo