1466-22-4

Upstream product

• 1617-18-1 ethyl 3-butenoate 
• 603-35-0 triphenylphosphine 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 122-78-1 phenylacetaldehyde 
• 41505-92-4 ethyl 2-(fluorosulfonyl)acetate 
• 100-44-7 benzyl chloride 
• 140-88-5 ethyl acrylate 
• 102575-03-1 ethyl (Z)-2-bromo-4-phenylbut-2-enoate 
• 71671-11-9 2-phenylethyl aci-nitronate 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 623-73-4 diazoacetic acid ethyl ester 
• 1530-45-6 (carbethoxymethyl)triphenylphosphonium bromide 
• 7605-25-6 ethyl phenylsulfenylacetate 
• 103-63-9 1-phenyl-2-bromoethane 

Downstream Products

• 42238-15-3 (2E)-4-phenylbut-2-en-1-ol 
• 180922-42-3 ethyl (2S,3R)-2-hydroxy-4-phenyl-3-(tosylamino)butanoate 
• 1205-84-1 ethyl (E)-4-phenylbut-3-enoate 
• 78000-63-2 ethyl (Z)-4-phenyl-3-butenoate 
• 869467-22-1 4-phenyl-3-sulfo-butyric acid ethyl ester 
• 884318-80-3 (R)-ethyl 3-(N-benzyl-N-((R)-1-phenylethyl)amino)-4-phenylbutanoate 
• 116949-67-8 (2S,3S)-2-azido-1-phenyl-butane-3,4-diol 
• 151250-78-1 Benzoic acid (2S,3S)-3-azido-2-hydroxy-4-phenyl-butyl ester 
• 140867-26-1 2(R)-<1'(S)-azido-2'-phenylethyl>oxirane 
• 136465-89-9 (2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane 
• 136465-96-8 3(S)-azido-4-phenyl-1-(p-toluenesulphonyloxy)-2(S)-butanol 
• 161170-92-9 (2S,3R)-2-Hydroxymethyl-3-phenylmethyloxirane 
• 245523-20-0 (2S,6S)-6-[(1S)-1-Azido-2-phenylethyl]-4-[(1S)-2-hydroxy-1-methylethyl]-2-methylmorpholin-3-one 
• 191217-12-6 (2S,3S)-3-Azido-1-[(1S)-2-(tert-butyldiphenylsilyloxy)-1-methylethylamino]-4-phenylbutan-2-ol 

Relevant academic research and scientific papers

Latent ruthenium-indenylidene catalysts bearing a N-heterocyclic carbene and a bidentate picolinate ligand

A silver-free methodology was developed for the synthesis of unprecedented N-heterocyclic carbene ruthenium indenylidene complexes bearing a bidentate picolinate ligand. The highly stable (SIPr)(picolinate)RuCl(indenylidene) complex 4a (SIPr = 1,3- bis(2-

Copper-Catalyzed Aerobic Oxidative Azo-Ene Cyclization

A copper-catalyzed aerobic oxidative azo-ene cyclization has been developed. The developed CuI/DMAP/O2 system efficiently facilitates the aerobic oxidation of ene-containing hydrazides to azo compounds, which undergo azo-ene cyclizations for the synthesis of oxazolidinones. In addition, the present approach enables the synthesis of lactams, as well as a nitroso-ene cyclization. Preliminary mechanistic studies revealed that two carbonyl groups were essential for the successful azo-ene cyclization and that a concerted mechanism might be plausible for this azo-ene cyclization. (Figure presented.).

Synthesis and self-photooxygenation of alkenyl-linked [60]fullerene derivatives. A regioselective ene reaction

(equation presented) Alkenyl-linked C60 derivatives undergo self-photooxygenation regioselectively, by the preferential abstraction of allylic hydrogens on the fullerene side of the double bond.

One-pot chemoenzymatic reactions in water enabled by micellar encapsulation

The use of micellar conditions to enable one-pot reactions involving both transition metal and enzymatic catalysts is reported. Representative enzymatic transformations under micellar conditions are unaffected by the presence of non-ionic surfactants, including designer surfactants such as TPGS-750-M. Furthermore, the presence of enzymes has a negligible effect on transition metal catalysis under micellar conditions in water. Finally, three one-pot chemoenzymatic reactions in water are reported in which the micelle-forming surfactant TPGS-750-M is a crucial factor for reaction efficiency.

Copper-Catalyzed Perfluoroalkylation of Allyl Phosphates with Stable Perfluoroalkylzinc Reagents

A general and practical method for copper-catalyzed cross-coupling of allyl phosphates with stable perfluoroalkylzinc reagents has been developed. The reaction proceeds under mild reaction conditions with high efficiency, good functional group tolerance, and high regio- A nd stereoselectivities and provides general, straightforward, and useful access to allyl-perfluoroalkyl compounds. Preliminary mechanistic studies reveal that the allyl copper intermediate may be involved in the catalytic cycle.

Tandem Remote Csp3-H Activation/Csp3-Csp3 Cleavage in Unstrained Aliphatic Chains Assisted by Palladium(II)

We report here a proof-of-concept for the cleavage of unstrained remote Csp3-Csp3 bonds at room temperature assisted by a directing group, opening up new possibilities to use aliphatic carboxylic acids as suitable alkenyl coupling partners. This strategy involves the Pd-mediated Csp3-H activation directed by a tethered 8-aminoquinoline group, followed by a concerted asynchronous carbene insertion into the Pd-C bond, and an unexpected β-carbon-carbon bond splitting. The insertion of a coupling partner into a Pd-C bond is a novel route to promote C-C bond cleavage, which in contrast to most common methodologies does not rely on the use of strained carbocycles.

Harnessing Secondary Coordination Sphere Interactions That Enable the Selective Amidation of Benzylic C-H Bonds

Engineering site-selectivity is highly desirable especially in C-H functionalization reactions. We report a new catalyst platform that is highly selective for the amidation of benzylic C-H bonds controlled by π-πinteractions in the secondary coordination sphere. Mechanistic understanding of the previously developed iridium catalysts that showed poor regioselectivity gave rise to the recognition that the π-cloud of an aromatic fragment on the substrate can act as a formal directing group through an attractive noncovalent interaction with the bidentate ligand of the catalyst. On the basis of this mechanism-driven strategy, we developed a cationic (ν5-C5H5)Ru(II) catalyst with a neutral polypyridyl ligand to obtain record-setting benzylic selectivity in an intramolecular C-H lactamization in the presence of tertiary C-H bonds at the same distance. Experimental and computational techniques were integrated to identify the origin of this unprecedented benzylic selectivity, and robust linear free energy relationship between solvent polarity index and the measured site-selectivity was found to clearly corroborate that the solvophobic effect drives the selectivity. Generality of the reaction scope and applicability toward versatile γ-lactam synthesis were demonstrated.

Organo-Catalyzed Regio- and Geometry-Specific Construction of β-Hydroxyl-α-vinyl Carboxylic Esters: Substrate Scope, Mechanistic Insights, and Applications

A green protocol has been developed for the synthesis of β-hydroxyl-α-vinyl carboxylic esters using aldehydes and α,β-unsaturated esters bearing an activated γ proton as starting materials under Morita-Baylis-Hillman (MBH) reaction conditions. Diverse β-hydroxyl-α-vinyl carboxylic esters have been synthesized regiospecifically in moderate to good yields with only E geometric selectivity. Other remarkable features include atom efficiency, environmental benignancy, and mild reaction conditions. Furthermore, the reaction products could be readily converted into tetrahydrofuran, dihydrofuran, and furan derivatives.

Discovery of Benzocycloalkane Derivatives Efficiently Blocking Bacterial Virulence for the Treatment of Methicillin-Resistant S. aureus (MRSA) Infections by Targeting Diapophytoene Desaturase (CrtN)

Antivirulence strategies are now attracting interest for the inherent mechanism of action advantages. In our previous work, diapophytoene desaturase (CrtN) was identified to be an attractive and drugable target for fighting pigmented S. aureus infections. In this research, we developed a series of effective benzocycloalkane-derived CrtN inhibitors with submicromolar IC50. Analogue 8 blocked the pigment biosynthesis of three MRSA strains with a nanomolar IC50 value. Corresponding to its mode of action, 8 did not function as a bactericidal agent. 8 could sensitize S. aureus to immune clearance. In vivo, 8 was proven to be efficacious in an S. aureus Newman sepsis model and abscess formation model. For two typical MRSAs, USA400 MW2 and Mu50, 8 significantly decreased the staphylococcal loads in the liver and kidneys. Moreover, 8 showed minimal antifungal activity compared to that of NTF. In summary, 8 has the potential to be developed as a therapeutic drug, especially against intractable MRSA issues.

Myoglobin-catalyzed olefination of aldehydes

The olefination of aldehydes constitutes a most valuable and widely adopted strategy for constructing carbon-carbon double bonds in organic chemistry. While various synthetic methods have been made available for this purpose, no biocatalysts are known to mediate this transformation. Reported herein is that engineered myoglobin variants can catalyze the olefination of aldehydes in the presence of α-diazoesters with high catalytic efficiency (up to 4,900 turnovers) and excellent Ediastereoselectivity (92-99.9 % de). This transformation could be applied to the olefination of a variety of substituted benzaldehydes and heteroaromatic aldehydes, also in combination with different alkyl α-diazoacetate reagents. This work provides a first example of biocatalytic aldehyde olefination and extends the spectrum of synthetically valuable chemical transformations accessible using metalloprotein-based catalysts.