87462-11-1

Upstream product

• 110-88-3 1,3,5-Trioxan 
• 100-42-5 styrene 
• 108-18-9 diisopropylamine 
• 50-00-0 formaldehyd 
• 4747-21-1 N-methylpropan-2-amine 
• 156370-50-2 N-isopropyl-2-phenylazetidine 
• 201230-82-2 carbon monoxide 
• 75-31-0 isopropylamine 
• 104-53-0 3-phenyl-propionaldehyde 
• 56146-87-3 N-isopropyl-3-phenylpropanamidate 
• 936-59-4 3-chloropropiophenone 
• 18776-12-0 3-chloro-1-phenyl-propan-1-ol 
• 23784-47-6 (2E)-N-isopropyl-3-phenylacrylamide 
• 1586-98-7 (2,3-dibromopropyl)benzene 

Downstream Products

• 883973-89-5 (S)-2-[3-Isopropyl-3-(3-phenyl-propyl)-ureido]-3-phenyl-propionic acid methyl ester 
• 883973-44-2 2-[3-isopropyl-3-(3-phenyl-propyl)-ureido]-N-methoxy-N-methyl-3-phenyl-propionamide 
• 883973-33-9 (S)-2-[3-Isopropyl-3-(3-phenyl-propyl)-ureido]-3-phenyl-propionic acid 

Relevant academic research and scientific papers

1,4-Palladium Shift/C(sp3)-H Activation Strategy for the Remote Construction of Five-Membered Rings

1,n-Metal shift is an elegant alternative approach enabling the functionalization of remote C-H bonds from simple precursors. In this work, we report a novel and simple Pd0-catalyzed domino reaction involving 1,4-palladium shift and C(sp3)-H activation and leading to (fused) five-membered rings. This method allowed access to a broad range of valuable arylidene γ-lactams and indanones and was applied to the formal synthesis of (-)-pyrrolam.

Practical regio- and stereoselective azidation and amination of terminal alkenes

There is significant interest in developing more rapid and efficient production of nitrogen-containing allylic compounds, as widely used in various syntheses. This work reports a variety of allylic azides and allylic amines synthesized by an efficient, new one-pot protocol that employs readily available terminal alkenes as starting materials. This method is highly regio- and stereoselective, affording the linear (E)-isomer, under metal-free conditions. This process tolerates several functional groups including halogen-containing molecules; it is general for azides and amine nucleophiles; and, adducts were obtained in good yields.

Synthesis of β-Lactams by Palladium(0)-Catalyzed C(sp3)?H Carbamoylation

A general and user-friendly synthesis of β-lactams is reported that makes use of Pd0-catalyzed carbamoylation of C(sp3)?H bonds, and operates under stoichiometric carbon monoxide in a two-chamber reactor. This reaction is compatible with a range of primary, secondary and activated tertiary C?H bonds, in contrast to previous methods based on C(sp3)?H activation. In addition, the feasibility of an enantioselective version using a chiral phosphonite ligand is demonstrated. Finally, this method can be employed to synthesize valuable enantiopure free β-lactams and β-amino acids.

Mild Metal-Free Hydrosilylation of Secondary Amides to Amines

The combination of amide activation by Tf2O with B(C6F5)3-catalyzed hydrosilylation with TMDS constitutes a method for the one-pot reduction of secondary amides to amines under mild conditions. The method displays a broad applicability for the reduction of many types of substrates, and shows good compatibility and excellent chemoselectivity for many sensitive functional groups. Reductions of a multifunctionalized α,β-unsaturated amide obtained from another synthetic methodology, and a C-H functionalization product produced the corresponding amines in good to excellent yield. Chemoselective reduction of enantiomeric pure (ee >99%) tetrahydro-5-oxo-2-furaneamides yielded 5-(aminomethyl)dihydrofuran-2(3H)-ones in a racemization-free manner. The latter were converted in one pot to N-protected 5-hydroxypiperidin-2-ones, which are building blocks for the synthesis of many natural products. Further elaboration of an intermediate led to a concise four-step synthesis of -epi-pseudoconhydrine.

Transformation of N,N-diisopropylarylmethylamines into N-isopropylarylmethylamines with molecular iodine

N,N-Diisopropylarylmethylamines were smoothly converted into the corresponding N-isopropylarylmethylamines by the reaction with molecular iodine in the presence of Na2CO3 in chloroform at 60 °C. Other related tertiary amines were also transformed into the corresponding secondary amines by the reaction with molecular iodine under the same reaction conditions.

Conventional and tandem hydroformylation

Transition-metal-catalyzed hydroformylation has become an essential tool for the synthesis of aldehydes. In this paper, we highlight several examples of synthetically useful applications of homogeneous and heterogeneous rhodium-catalyzed hydroformylation, as well as several examples of tandem processes involving hydroformylation as a reaction step developed in our laboratory.

Practical access to amines by platinum-catalyzed reduction of carboxamides with hydrosilanes: Synergy of dual Si-H groups leads to high efficiency and selectivity

The synergetic effect of two Si-H groups leads to efficient reduction of carboxamides to amines by platinum catalysts under mild conditions. The rate of the reaction is dependent on the distance of two Si-H groups; 1,1,3,3-tetramethyldisiloxane (TMDS) and 1,2-bis(dimethylsilyl)benzene are found to be an effective reducing reagent. The reduction of amides having other reducible functional groups such as NO2, CO2R, CN, CdC, Cl, and Br moieties proceeds with these groups remaining intact, providing a reliable method for the access to functionalized amine derivatives. The platinum-catalyzed reduction of amides with polymethylhydrosiloxane (PMHS) also proceeds under mild conditions. The reaction is accompanied by automatic removal of both platinum and silicon wastes as insoluble silicone resin, and the product is obtained by simple extraction. A mechanism involving double oxidative addition of TMDS to a platinum center is discussed.

The ruthenium-catalyzed reduction and reductive N-alkylation of secondary amides with hydrosilanes: Practical synthesis of secondary and tertiary amines by judicious choice of hydrosilanes

(Chemical Equation Presented) A triruthenium cluster, (μ3, η2,η3,η5-acenaphthylene)Ru 3(CO)7 (1) catalyzes the reaction of secondary amides with hydrosilanes, yielding a mixture of secondary amines, tertiary amines, and silyl enamines. Production of secondary amines with complete selectivity is achieved by the use of higher concentration of the catalyst (3 mol %) and the use of bifunctional hydrosilanes such as 1,1,3,3-tetramethyldisiloxane. Acidic workup of the reaction mixture affords the corresponding ammonium salts, which can be treated with a base, providing a facile method for isolation of secondary amines with high purity. In contrast, tertiary amines are formed with high selectivity by using lower concentration of the catalyst (1 mol %) and polymeric hydrosiloxanes (PMHS) as reducing agent. Reduction with PMHS encapsulates the ruthenium catalyst and organic byproducts to the insoluble silicone resin. The two reaction manifolds are applicable to various secondary amides and are practical in that the procedures provide the desired secondary or tertiary amine as a single product. The product contaminated with only minimal amounts of ruthenium and silicon residues. On the basis of the products and observed side products as well as NMR studies a mechanistic scenario for the reaction is also described.

A novel series of urea-based peptidomimetic calpain inhibitors

A series of peptide aldehyde derivatives in which the P2 chiral carbon has been replaced with nitrogen were synthesized as urea-based peptidomimetic inhibitors of μ-calpain. The compounds mirrored the general SAR of peptidyl aldehyde calpain inhibitors but displayed greater selectivity for μ-calpain over cathepsin B.

Synthesis of N,N′,N″-trisubstituted thiourea derivatives and their antagonist effect on the vanilloid receptor

Twenty-seven N,N′,N″-trisubstituted thiourea derivatives were prepared. Among them, 1-[3-(4′-hydroxy-3′-methoxy-phenyl)-propyl]-1,3-diphenethyl- thiourea (8l, IC50=0.32 μM), showed 2-fold higher antagonistic activity than that of capsazepine (3