51491-77-1

Upstream product

• 18159-22-3 1-benzyl-1H-pyrrole-2-carboxylic acid 
• 18159-23-4 1-benzylpyrrole-2-carboxylic acid methyl ester 

Downstream Products

• 108832-28-6 [5-(1-Benzyl-1H-pyrrole-2-carbonyl)-1,4-dimethyl-1H-pyrrol-2-yl]-acetic acid 
• 1252611-89-4 (R,Z)-1-(1-benzyl-1H-pyrrol-2-yl)-2-(2-methylpropylidene)-3-(2-oxo-4-phenyloxazolidin-3-yl)propane-1,3-dione 
• 1252611-97-4 ethyl (2Z)-2-(1-benzyl-1H-pyrrole-2-carbonyl)-4-methylpent-2-enoate 
• 1252612-26-2 (S,Z)-1-(1-benzyl-1H-pyrrol-2-yl)-2-benzylidene-3-(2-oxo-4-phenyloxazolidin-3-yl)propane-1,3-dione 
• 1370641-36-3 (S,Z)-3-[1-(1-benzyl-1H-pyrrol-2-yl)-4-methyl-1-oxopent-2-en-2-yl]-4-phenyloxazolidin-2-one 
• 1370641-15-8 (S)-3-{(4S,5R)-1-benzyl-4-isopropyl-6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrol-5-yl}-4-phenyloxazolidin-2-one 

Relevant academic research and scientific papers

Catalyst-Controlled Chemodivergent Reactions of 2-Pyrrolyl-α-diazo-β-ketoesters and Enol Ethers: Synthesis of 1,2-Dihydrofuran Acetals and Highly Substituted Indoles

A catalyst-controlled, chemodivergent reaction of pyrrolyl-α-diazo-β-ketoesters with enol ethers is reported. While Cu(II) catalysts selectively promoted a [3 + 2] cycloaddition to provide pyrrolyl-substituted 2,3-dihydrofuran (DHF) acetals, dimeric Rh(II) catalysts afforded 6-hydroxyindole-7-carboxylates via an unreported [4 + 2] benzannulation. The choice of enol ether proved to be crucial in determining both regioselectivity and yield of the respective products (up to 91% yield for Cu(II) and 82% for Rh(II) catalysis). Furthermore, the DHF acetals were shown to serve as precursors to 7-hydroxyindole-6-carboxylates (isomeric to the indoles formed from Rh) and highly substituted furans in the presence of Lewis acids. Thus, from a common pyrrolyl-α-diazo-β-ketoester, up to three unique heterocyclic scaffolds can be achieved based on catalyst selection.

A reductive-coupling plus nazarov cyclization sequence in the asymmetric synthesis of five-membered carbocycles

Palladium-mediated hydrostannylation of alkynoyl compounds is combined with Stille-Scott cross-coupling (reductive-coupling) to give one-pot access to divinyl and aryl vinyl ketones, which undergo Nazarov cyclization to give cyclopentenones upon treatment with acid. This reaction sequence has been studied with a variety of different substitution patterns, including the use of oxazolidinone auxiliaries to achieve torquoselectivity in the Nazarov cyclization. Through a combination of good yields and moderate to good levels of stereochemical induction, this approach affords efficient, convergent, and asymmetric access to a variety of different cyclopentanoid systems.