20840-08-8

Upstream product

• 7143-76-2 cyclopropyl-p-tolyl-methanone 
• 101971-33-9 trans-3-chloro-2-p-tolylphenyltetrahydrofuran 
• 627-27-0 homoalylic alcohol 
• 106-38-7 para-bromotoluene 
• 31208-53-4 4-p-tolylbut-3-yn-1-ol 
• 1191-99-7 2,3-dihydro-2H-furan 
• 380481-66-3 5,5-dimethyl-2-(4-methylphenyl)-1,3,2-dioxaborinane 
• 1250907-64-2 methyl (E)-4-(p-tolyl)but-3-enoate 
• 127404-74-4 (E)-4-(4-tolyl)-3-butenoic acid 
• 51114-94-4 (2-carboxyethyl)triphenylphosphonium bromide 
• 763-32-6 2-methyl-1-buten-4-ol 
• 101671-00-5 (E)-2-(4-methylphenyl)-1-nitroethene 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 603-35-0 triphenylphosphine 

Downstream Products

• 1352632-29-1 C₂₀H₁₈ClNO 
• 1352632-30-4 C₂₁H₂₀ClNO 
• 1224951-97-6 (E)-4-(4-methylphenyl)but-3-enyl methanesulfonate 
• 1426692-49-0 3-chloro-2-p-tolyltetrahydrofuran 

Relevant academic research and scientific papers

A Mechanistically Inspired Halenium Ion Initiated Spiroketalization: Entry to Mono- and Dibromospiroketals

Employing halenium affinity (HalA) as a guiding tool, the weak nucleophilic character of alkyl ketones was modulated by the templating effect of a tethered 2-tetrahydropyranyl(THP)-protected alcohol towards realizing a bromenium ion initiated spiroketaliz

Intramolecular N-Me and N-H aminoetherification for the synthesis ofN-unprotected 3-amino-O-heterocycles

A mild Rh-catalyzed method for synthesis of cyclic unprotected N-Me and N-H 2,3-aminoethers using an olefin aziridination-aziridine ring-opening domino reaction has been developed. The method is readily applicable to the stereocontrolled synthesis of a va

An Enzymatic Platform for the Highly Enantioselective and Stereodivergent Construction of Cyclopropyl-δ-lactones

Abiological enzymes offers new opportunities for sustainable chemistry. Herein, we report the development of biological catalysts derived from sperm whale myoglobin that exploit a carbene transfer mechanism for the asymmetric synthesis of cyclopropane-fused-δ-lactones, which are key structural motifs found in many biologically active natural products. While hemin, wild-type myoglobin, and other hemoproteins are unable to catalyze this reaction, the myoglobin scaffold could be remodeled by protein engineering to permit the intramolecular cyclopropanation of a broad spectrum of homoallylic diazoacetate substrates in high yields and with up to 99 % enantiomeric excess. Via an alternate evolutionary trajectory, a stereodivergent biocatalyst was also obtained for affording mirror-image forms of the desired bicyclic products. In combination with whole-cell transformations, the myoglobin-based biocatalyst was used for the asymmetric construction of a cyclopropyl-δ-lactone scaffold at a gram scale, which could be further elaborated to furnish a variety of enantiopure trisubstituted cyclopropanes.

Dealkenylative Alkenylation: Formal σ-Bond Metathesis of Olefins

The dealkenylative alkenylation of alkene C(sp3)?C(sp2) bonds has been an unexplored area for C?C bond formation. Herein 64 examples of β-alkylated styrene derivatives, synthesized through the reactions of readily accessible feedstock olefins with β-nitrostyrenes by ozone/FeII-mediated radical substitutions, are reported. These reactions proceed with good efficiencies and high stereoselectivities under mild reaction conditions and tolerate an array of functional groups. Also demonstrated is the applicability of the strategy through several synthetic transformations of the products, as well as the syntheses of the natural product iso-moracin and the drug (E)-metanicotine.

Highly E-Selective, Stereoconvergent Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Alkenyl Ethers

An improved method for the nickel-catalyzed Suzuki-Miyaura cross-coupling of alkenyl ethers is reported. This stereoconvergent protocol allows for the utilization of a wide range of alkenyl ethers and aryl boronic esters for the synthesis of variously sub

Hypervalent iodine initiated intramolecular alkene dimerisation: A stereodivergent entry to cyclobutanes

The emergence of new methods for the stereoselective synthesis of strained carbocycles is a challenging but worthwhile endeavour. Cyclobutanes, in particular, have attracted the attention of both medicinal chemists and material scientists for their unique properties. Herein, we present a new method that allows access to highly functionalized cyclobutanes with complementary all-trans and trans-cis-trans relative stereochemistry, that could not be accessed before. This approach consists of an intramolecular dimerisation of non-conjugated dienes using an oxidative single electron transfer (SET) process, and is initiated by catalytic amounts of hypervalent iodine reagents. The potential uses of these cyclobutanes is demonstrated with selective functionalization, including the formation of diols and carboxylic acids.

Nickel-catalyzed ring-opening cross-coupling of cyclic alkenyl ethers with arylboronic esters via carbon-oxygen bond cleavage

We have developed a nickel-catalyzed cross-coupling reaction of cyclic alkenyl ethers with arylboronic esters that leads to the formation of unsaturated alcohols via ring-opening by the cleavage of a C(sp2)-O bond. The use of 1,3-dicyclohexylimidazol-2-ylidene as the ligand is essential to promote this cross-coupling process.

Asymmetric 5-endo chloroetherification of homoallylic alcohols toward the synthesis of chiral β-chlorotetrahydrofurans

An asymmetric 5-endo chloroetherification of homoallylic alcohols is successfully developed that employs an easily available quaternary ammonium salt derived from cinchonine as a conventional organocatalyst. This approach provides ready access to β-chloro

Application of sulfuryl chloride for the quick construction of β-chlorotetrahydrofuran derivatives from homoallylic alcohols under mild conditions

An efficient and mild method is reported for the construction of β-chlorotetrahydrofuran derivatives by 5-endo chlorocycloetherification of homoallylic alcohols. The system employs sulfuryl chloride as the chlorinating agent under catalyst-free conditions. A variety of homoallylic alcohols with aryl or alkyl substituents were smoothly converted into β- chlorotetrahydrofurans in yields up to 98%.

Oxidative Mizoroki-Heck-type reaction of arylsulfonyl hydrazides for a highly regio- and stereoselective synthesis of polysubstituted alkenes

A useful source: Arylsulfonyl hydrazides have been identified as synthetically useful aryl sources for the Pd(OAc)2 catalyzed oxidative Mizoroki-Heck-type reaction under molecular oxygen to provide a convenient access to polysubstituted alkenes in a highly regio- and stereoselective manner (see scheme). The reaction well tolerates various functional groups such as alkoxy, halo, alcohol, carboxylic acid, ester, amide, sulfonamide, and sulfone. Copyright