89649-58-1

Upstream product

• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 
• 89649-30-9 4'-Methyl-2'-phenyl-2,3,4,5,2',3'-hexahydro-1'H-[1,2']bipyrrolyl-5'-carboxylic acid methyl ester 
• 32740-84-4 methyl 3-methyl-2H-azirine-2-carboxylate 
• 623-43-8 methyl crotonate 
• 158630-19-4 4-acetamido-4,4-diethoxycarbonyl-3-methyl-1-phenylbutan-1-one 
• 495-41-0 1-phenylbut-2-en-1-one 
• 405551-14-6 methyl (E)-2-(N-benzhydrylideneamino)-5-phenyl-3-methylpent-4-enoate 
• 405551-16-8 methyl (E)-2-amino-3-methyl-5-phenylpent-4-enoate 
• 163807-60-1 ethyl (E)-3-phenyl-1-methylprop-1-enyl carbonate 
• 405551-17-9 methyl (E)-3-methyl-5-phenyl-2-(4-tolylsulfonylamino)pent-4-enoate 

Relevant academic research and scientific papers

The synthesis of 5-substituted proline derivatives and of 5-substituted pyrrole-2-carboxylates by 5-endo cyclisations featuring a method for effectively favouring these with respect to 5-exo cyclisations

Overall 5-endo cyclisations of the C-allylic glycine sulfonamides 5 lead to usually excellent yields of the 2,5-cis- or 2,5-trans-pyrrolidine-2-carboxylates 11 and 12 respectively, depending upon whether base is absent or present. While reductions to the corresponding pyrrolidine-2-methanols 13 proved efficient, subsequent eliminations of the elements of hydrogen iodide gave mixtures of products 14-16. Suitably positioned hydroxy groups compete successfully with the sulfonamide via a 5-exo cyclisation mode. However, when such a substrate contains a furan ring attached to the alkene function (21), then cyclisation does occur at the sulfonamide, presumably by participation of the furan oxygen, to give an iodopyrrolidine-2-methanol 13a. Finally, base-induced elimination of both hydrogen iodide and toluene-p-sulfinic acid from the initial iodopyrrolidines 11 and 12 leads to 5-substituted pyrrole-2-carboxylates 26. Overall, this sequence is complementary to the Kenner pyrrole synthesis.

A new approach to 5-substituted prolines and 2-pyrrolecarboxylates

Iodocyclisations of the allylic glycinates 7 lead either to the trans- or cis-2,5-disubstituted proline derivatives 8 or 9, depending on the reaction conditions; subsequent treatment of these with DBU in DMF gives the 2-pyrrolecarboxylates 10 and 13 in excellent yields by a double elimination of hydrogen iodide and toluenesulfinic acid.

Double diastereoselectivite de la cycloaddition dipolaire-1,3 d'ylures d'azomethine cycliques substitues

Seven derivatives of methyl 5-phenyl-3,4-dihydro-2H-pyrrole-2-carboxylates 1 were synthesized.These compounds are precursors of pentagonal cyclic azomethine ylides, the two sides of which are diastereotopic.The 1,3-dipolar species react with N-methyl and

The Synthesis and Chemistry of Azolenines. Part 2. A General Synthesis of Pyrrole-2-carboxylic Acid Derivatives by the Reaction of 2H-Azirines with Enamines, and the Crystal and Molecular Structure of Ethyl 3-Phenyl-4,5,6,7-tetrahydroindole-2-carboxylate

A new general synthesis of 1H-pyrrole-2-carboxylic acid derivatives is described.Reaction between appropriately substituted 2H-azirines and enamines gives a mixture of 2,3- and 3,4-dihydropyrroles, which on acid treatment yields the title compounds in mod