55164-54-0

Upstream product

• 402938-21-0 (Z)-methyl 3-[[(1,1-dimethylethoxycarbonyl)methylamino]methyl]-3-phenyl-2-propenoate 
• 1105662-87-0 tert-butyl 3-(2-methoxy-2-oxo-ethylidene)azetidine-1-carboxylate 
• 143704-79-4 (Z)-ethyl 4-bromo-3-phenylbut-2-enoate 
• 74-89-5 methylamine 
• 945-93-7 ethyl (E)-3-phenylbut-2-enoate 
• 154026-89-8 (Z)-methyl 3-iodo-3-phenyl-propenoate 
• 536-74-3 phenylacetylene 
• 4891-38-7 phenylpropynoic acid methyl ester 

Downstream Products

• 13217-97-5 1-methyl-3-phenyl-1H-pyrrole 

Relevant academic research and scientific papers

Rhodium catalyzed C-C bond cleavage/coupling of 2-(azetidin-3-ylidene)acetates and analogs

The C-C bond cleavage/coupling of 2-(azetidin-3-ylidene)acetates with aryl boronic acids catalyzed by a rhodium complex was studied with a "conjugate addition/β-C cleavage/protonation" strategy.

Iron-catalyzed aerobic C-H functionalization of pyrrolones

The aerobic oxidation of pyrrolones catalyzed by Fe(OTf)3 to form reactive N-acyliminium ion intermediates that undergo nucleophilic additions with alcohols to give the corresponding products in moderate to good yields is described.

α-(N-carbamoyl)alkylcuprate chemistry in the synthesis of nitrogen heterocycles

The conjugate adducts obtained via coupling of α-(N-carbamoyl)alkylcuprates with α,β-ynoates, α-allenyl esters, or α,β-enoates or enimides undergo N-Boc deprotection and cyclization onto the ester functionality upon treatment with PhOH/TMSCl, catecholboron bromide, or trimethylsilyl triflate. This two-pot sequence provides synthetic routes to 4-alkylidinepyrrolidine-2-ones, 4-alkylidinepyrrolizidin-2-ones, and 4-alkylidineindolizidin-2-ones via allenyl esters; pyrrolin-2-ones, tetrahydropyrrolizin-2-ones, and tetrahydroindolizin-2-ones via α,β-ynoates; pyrrolidin-2-ones, pyrrolizidin-2-ones, and indolizidin-2-ones via α,β-enoates or α,β-enimides. The reluctance of γ-carbamoyl-α,β-enoates to undergo E/Z isomerization requires the use of (Z)-β-iodo-α,β-enoates readily prepared by the addition of HI to the alkynyl esters for the efficient preparation of pyrrolinones, tetrahydropyrrolizinones, and tetrahydroindolizinones. Utilization of ω-functionalized α,β-ynoates or β-iodo-α,β-enoates allows for cyclization onto the ω-functionality providing for a synthetic route to quinolizidines.