110426-80-7

Upstream product

• 72707-66-5 2-(bromomethyl)acrylic acid 
• 873-55-2 sodium benzenesulfonate 
• 108-18-9 diisopropylamine 
• 36526-15-5 3-(phenylsulfonyl)-2-methylenepropanoic acid 

Downstream Products

• 119039-04-2 N,N-diisopropyl-4-benzoyl-4-methylcyclopent-1-ene-carboxamide 
• 119039-06-4 N,N-diisopropyl-4-(phenylsulfonyl)-4-methylcyclopent-1-enecarboxamide 
• 105970-95-4 N,N-diisopropyl-N'-methyl-N'-phenyl-1-cyclopentene-1,3-dicarboxamide 
• 105970-96-5 N,N-diisopropyl-N'-methyl-N'-phenyl-1-cyclopentene-1,4-dicarboxamide 
• 119039-07-5 2-((Z)-4-Benzenesulfonyl-3-diisopropylcarbamoyl-1-phenyl-but-2-enyl)-malonic acid diethyl ester 
• 119039-16-6 (E)-2-[1-Benzenesulfonyl-meth-(Z)-ylidene]-4-phenyl-but-3-enoic acid diisopropylamide 
• 110426-81-8 N,N-diisopropyl-4-<(cyclohexyloxy)carbonyl>-4-methylcyclopent-1-ene-carboxamide 

Relevant academic research and scientific papers

An Anionic 3 + 2 Cyclization-Elimination Route to Cyclopentenes

The formation and reactions of lithium (10) are reported.When 10 is allowed to react with olefins bearing an electron-withdrawing group the 4-substituted cyclopent-1-enecarboxamides 11-19 are produced in 22-89percent yields.Methyl-substituted analogues of 10, the allyllithium reagents 23 and 25, react in a similar manner to produce cyclopentenes that have methyl groups in the 2 or 5 positions.The corresponding lithium and lithium reagents also react with electron-deficient olefins to produce the substituted cyclopentenes 28 and 30, which can be hydrolyzed readily to the carboxylic acid 42.The formation of the cyclopentenes occurs in a stepwise fashion by an initial highly regioselective addition to the electron-deficient olefin by the allyllithium reagent followed by a 5-Endo-Trig cyclization and elimination of benzenesulfinate.The allyllithium 10 undergoes polydeuteration on reaction with methanol-O-d and acetone-d6, alkylation with methyl iodide, and addition-dehydratation on reaction with benzaldehyde.

AN ANIONIC 3+2 CYCLIZATION-ELIMINATION ROUTE TO CYCLOPENTENES

Anionic 3+2 cyclization-elimination reactions between 1-benzenesulfonyl-2-(N,N-diisopropyl)carboxamidoallyllithium (2) and electron-deficient olefins provide the 4-substituted-N,N-diisopropylcyclopent-1-ene carboxamides 3-8 in yields of 22-89percent.