88381-98-0

Upstream product

• 24850-33-7 allyltributylstanane 
• 780-25-6 N-benzylidene benzylamine 
• 106-95-6 allyl bromide 
• 1594-94-1 allyl dimethyl boronic acid ester 
• 58044-89-6 N,N-dibenzyl-1,1,1-trifluoromethanesulfonamide 
• 2622-05-1 allylmagnesium bromide 
• 762-72-1 allyl-trimethyl-silane 
• 27845-50-7 (E)-N-benzylidenebenzylamine 
• 1730-25-2 allylmagnesium bromide 
• 100-52-7 benzaldehyde 
• 100-46-9 benzylamine 
• 2551-83-9 allyltrimethoxysilane 
• 1746-13-0 allyl phenyl ether 
• 103-49-1 dibenzylamine 

Downstream Products

• 188302-67-2 1-Benzyl-4-bromo-2-phenyl-pyrrolidine 
• 431982-25-1 N-benzyl-N-(1-phenylbut-3-enyl)acrylamide 
• 243656-96-4 N-benzyl-N-(1-phenylbut-3-enyl)acetamide 
• 431982-26-2 N-benzyl-2-methyl-N-(1-phenylbut-3-enyl)acrylamide 
• 107520-59-2 N-Benzyl-5,6-dihydro-6-phenyl-2(1H)-pyridinone 

Relevant academic research and scientific papers

Concurrent Formation of N-H Imines and Carbonyl Compounds by Ruthenium-Catalyzed C-C Bond Cleavage of β-Hydroxy Azides

A commercial cyclopentadienylrutenium dicarbonyl dimer ([CpRu(CO)2]2) efficiently catalyzes the formation of N-H imines and carbonyl compounds simultaneously from β-hydroxy azides via C-C bond cleavage under visible light. Density functional theory calculations for the cleavage reaction support the mechanism involving chelation of alkoxy azide species and liberation of nitrogen as the driving force. The synthetic utility of the reaction was demonstrated by a new amine synthesis promoted by chemoselective allylation of imine and synthesis of isoquinoline.

Iridium-Catalyzed Reductive Nucleophilic Addition to Secondary Amides

An iridium-catalyzed reductive nucleophilic addition to secondary amides is reported. After the iridium-catalyzed reduction, the resulting imines can undergo the Strecker reaction, the Mannich reaction, allylation, and [3 + 2]-cycloaddition. The method sh

Iridium-Catalyzed Reductive Alkylations of Secondary Amides

Reported herein is the first direct, metal-catalyzed reductive functionalization of secondary amides to give functionalized amines and heterocycles. The method is shown to have exceptionally broad scope with respect to suitable nucleophiles, which cover both hard and soft C nucleophiles as well as a P nucleophile. The reaction exhibits good chemoselectivity and tolerates several sensitive functional groups.

One-Pot Reductive Allylation of Amides by Using a Combination of Titanium Hydride and an Allylzinc Reagent: Application to a Total Synthesis of (-)-Castoramine

A one-pot direct reductive allylation protocol has been developed for the synthesis of secondary amines by using titanium hydride and an allylzinc reagent. This protocol is applicable to a broad range of substrates, including acyclic amides, benzamides, α,β-unsaturated amides, and lactams. The stereochemical outcome obtained from the reaction with crotylzinc reagent suggested that the allylation reaction proceeds through a six-membered cyclic transition state. A total synthesis of (-)-castoramine was accomplished by following this protocol for the highly stereoselective construction of contiguous stereocenters.

Synthesis of Cyclic Guanidines Bearing N-Arylsulfonyl and N-Cyano Protecting Groups via Pd-Catalyzed Alkene Carboamination Reactions

Palladium-catalyzed carboamination reactions of N-allylguanidines bearing cleavable N-cyano or N-arylsulfonyl protecting groups are described. The reactions afford cyclic guanidine products in good yield, and transformations of substrates bearing internal alkenes proceed with high diastereoselectivity. Deuterium labeling studies indicate these transformations proceed via anti-aminopalladation pathways.

Dimethylzinc-Mediated Chlorolactamization of Homoallylic Amines with Chloroform

A novel chlorolactamization reaction of homoallylic amines has been developed. The treatment of homoallylic amines with dimethylzinc in chloroform led to the formation of the corresponding β-chlorolactams via the Prins-type cyclization of a carbamoyl chlo

Efficient synthesis of homoallylic alcohols/amines from allyltributylstannane and carbonyl compounds/imines using iodine as catalyst under acetic acid-water medium

This paper describes a general method for the synthesis of homoallylic alcohols and amines by nucleophilic addition reaction of allyltributylstannane to carbonyl compounds and aldimines where iodine acts as a catalyst in H2O/acetic acid (1:1) medium. Only 10 mol% of I2 is required for various organic transformations. By using this process, various homoallylic alcohols and amines are produced in good to excellent yields.

Synthesis of polysubstituted pyrroles via Pd-catalyzed oxidative alkene C-H bond arylation and amination

A novel Pd(II)-catalyzed oxidative approach to construct polysubstituted pyrroles from N-homoallylicamines and arylboronic acids was developed. This transformation is supposed to proceed through cascade formation of C-C and C-N bonds via oxidative arylation of unactive alkenes, followed by intramolecular aza-Wacker cyclization.

Aza-[2,3]-Wittig Sigmatropic Rearrangement of Allylic Tertiary Amines: A Successful Example with High Chirality Transfer

We report herein a successful example of an aza-[2,3]-Wittig rearrangement in an allylic tertiary N,N-dibenzyl amine derived from (S)-alaninol or (S)-isoleucinol. This reaction occurs upon metalation at the benzylic position with a mixture of butyllithium/diisopropylamine/potassium t-butoxide and proceeds with a high 1,3 transfer of chirality.

Chemoselective reductive nucleophilic addition to tertiary amides, secondary amides, and N-methoxyamides

As the complexity of targeted molecules increases in modern organic synthesis, chemoselectivity is recognized as an important factor in the development of new methodologies. Chemoselective nucleophilic addition to amide car-bonyl centers is a challenge because classical methods require harsh reaction conditions to overcome the poor elec-trophilicity of the amide carbonyl group. We have successfully developed a reductive nucleophilic addition of mild nu-cleophiles to tertiary amides, secondary amides, and N-methoxyamides that uses the Schwartz reagent [Cp2ZrHCl]. The reaction took place in a highly chemoselective fashion in the presence of a variety of sensitive functional groups, such as methyl esters, which conventionally require protection prior to nucleophilic addition. The reaction will be applicable to the concise synthesis of complex natural alkaloids from readily available amide groups.