120318-54-9

Upstream product

• 68843-72-1 ethyl 2-aminopent-4-enoate 
• 98-59-9 p-toluenesulfonyl chloride 
• 107-18-6 allyl alcohol 
• 1253966-28-7 4-ethyloxy-1-(4-methylbenzenesulfonyl)-1,2,3-triazole 
• 115289-57-1 ethyl N-(diphenylmethylene)-2-amino-4-pentenoate 

Downstream Products

• 271598-79-9 ethyl 2-{[(4-methylphenyl)sulfonyl](prop-2-ynyl)amino}pent-4-enoate 
• 1025765-55-2 C₂₀H₂₉NO₄S 
• 1025765-54-1 C₁₉H₂₇NO₄S 
• 1025765-53-0 C₁₈H₂₅NO₄S 
• 271599-10-1 ethyl N-[(4-methylphenyl)sulfonyl]-5-vinyl-1,2,3,6-tetrahydropyridine-2-carboxylate 
• 271598-82-4 ethyl 2-{[(4-methylphenyl)sulfonyl](3-trimethylsilylprop-2-ynyl)amino}pent-4-enoate 

Relevant academic research and scientific papers

One-pot procedure for the introduction of three different bonds onto terminal alkynes through N-sulfonyl-1,2,3-triazole intermediates

Triple strike: Copper(I) and rhodium(II) complexes can cooperate to facilely convert terminal alkynes into α-allyl-α-amino ketones through triazole intermediates. This synthetic process achieves the regioselective multifunctionalization of terminal alkyne

Synthesis of 2-Substituted 2-Amino Ketones by Rhodium-Catalyzed Reaction of N-Sulfonyl-1,2,3-triazoles with 2-Alkenols

A study on a rhodium(II)-catalyzed reaction of N-sulfonyl-1,2,3-triazoles with 2-alkenols is reported. The reaction is initiated by insertion of an α-imino carbene into the O–H linkage of alcohol, forming a 2-alkenoxy enamide intermediate. A thermal [3,3]-sigmatropic rearrangement follows to yield 2-substituted 2-amino ketone in a stereoselective manner. The successful application of this methodology to a formal synthesis of (–)-α-conhydrine is also described.

One-Step Ruthenium-Catalysed Transformation of 1,7-Enynes into Strained Bicyclic Amino Esters

The reaction of 1,7-enynes, synthesised from α-amino acids, carried out with diazo compounds in the presence of the Cp*RuCl(cod) catalyst allowed the one-step preparation of various strained bicyclic pipecolic acid derivatives in good yields under mild conditions. The stereoselectivity of the created double bond depends on the nature of the diazoalkane, and the diastereoselectivity arises essentially from steric factors.

Synthesis of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives by cycloaddition approaches

A new and general synthetic methodology for the preparation of functionalized 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives by a cycloaddition strategy is described. The synthesis of various enyne building blocks 12, 13, 21, and 22 containing an α-amino acid moiety using Schiff base 8 as a glycine equivalent has been achieved under mild reaction conditions. These building blocks have been utilized in the synthesis of inner-outer ring dienes 23 and 24 and exocyclic dienes 26 and 29, the key steps being an enyne metathesis reaction and cycloisomerization. Various topographically constrained Tic derivatives have been synthesized using dienes containing an α-amino acid moiety through Diels-Alder reactions. For the first time, [2+2+2] cyclotrimerization, as promoted by Wilkinson's and Vollhardt's catalysts, has been used for the synthesis of various highly functionalized Tic derivatives.

A new synthetic approach to 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives via enyne metathesis and the Diels-Alder reaction

Various substituted 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives are synthesized via enyne metathesis and the Diels-Alder reaction.