191215-86-8

Upstream product

• 591-50-4 iodobenzene 
• 191215-76-6 methyl 2-[(4-toluenesulfonyl)amino]-4-pentynoate 
• 167904-79-2 methyl (R,S)-2-(N-diphenylmethylidene)aminopent-4-ynoate 
• 23235-02-1 N-Acetyl-α-propargylglycine 
• 61172-60-9 diethyl α-acetamido-α-propargylmalonate 
• 166271-28-9 2-amino-pent-4-ynoic acid methyl ester hydrochloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 70837-20-6 propargyclycine methyl ester hydrochloride 

Downstream Products

• 216988-56-6 methyl 4-iodo-5-phenyl-1-(4-tolylsulfonyl)-2,3-dihydropyrrole-2-carboxylate 
• 191215-77-7 2-[N-(toluene-4-sulfonyl)-N-(prop-2-enyl)amino]-5-phenylpent-4-ynoic acid methyl ester 

Relevant academic research and scientific papers

Gold-Catalyzed Cycloisomerization of Alkyne-Containing Amino Acids: Controlled Tuning of C–N vs. C–O Reactivity

Versatile alkyne-containing amino acids were used as ambident precursors in the divergent synthesis of alkylidenelactones and 1-pyrrolines. Two gold-catalyzed protocols were applied for selective intramolecular O- and N-cycloisomerization reactions.

Pd-Catalysed Synthesis of 5-Substituted Proline Derivatives from Acetylene-Containing Amino Acids

2,5-Disubstituted pyrrolines have been synthesised via Pd-catalysed 5-endo-dig cyclisations of substituted acetylene-containing amino acids. It has also been shown that these pyrrolines can be efficiently transformed into the corresponding saturated proli

An approach to 2,3-dihydropyrroles and β-iodopyrroles based on 5-endo-dig cyclisations

A representative series of homopropargylic sulfonamides 19 and 22b have been found to undergo smooth 5-endo-dig cyclisation upon exposure to excess iodine in acetonitrile containing potassium carbonate. The resulting 4-iodo-2,3-dihydropyrroles 23 readily react with two equivalents of DBU in DMF at 20°C to give the corresponding β-iodopyrroles 24 and 26 in excellent yields by the elimination of toluene-p-sulfinic acid. Use of less than two equivalents of base results in some loss of iodine. The iodo-2,3-dihydropyrroles 23 can be used in palladium-catalysed coupling reactions as shown by the efficient formation of the Sonogashira product 29 under mild conditions.

5-Endo-dig cyclisations of homopropargylic sulfonamides: A new route to 2,3-dihydropyrroles and β-iodopyrroles

5-endo-dig Iodocyclisations of the homopropargylic sulfonamides 12a-c and 13 give excellent yields of the iododihydropyrroles 14a-d and thence the β-iodopyrroles 15a-d, following base-catalysed elimination of sulfinic acid.

Solid phase synthesis of fused bicyclic amino acid derivatives via intramolecular Pauson-Khand cyclization: Versatile scaffolds for combinatorial chemistry

Solution and solid phase synthetic methods leading to the rapid, stereocontrolled construction of highly functionalized fused bicyclic amino acid derivatives have been developed. The key step involves a unique application of the intramolecular Pauson-Khand cyclization for the construction of hexahydro-1H-[2]pyrindinone ring systems. Further modifications which demonstrate the potential for combinatorial library generation are also disclosed.