4255-32-7

Upstream product

• 53979-32-1 2-(4-methoxy-benzyl)-pent-4-enoic acid 
• 1448804-69-0 (±)-tert-butyl (1-(4-methoxyphenyl)pent-4-en-2-yl)carbamate 
• 2746-25-0 p-Methoxybenzyl bromide 
• 503025-43-2 1-(4-methoxyphenyl)pent-4-en-2-ol 
• 5703-26-4 4-Methoxyphenylacetaldehyde 

Downstream Products

• 1399639-02-1 C₁₉H₁₈N₂O₆S 
• 1448804-70-3 C₁₉H₂₁N₃O₆S 

Relevant academic research and scientific papers

Catalyst-controlled C-O versus C-N allylic functionalization of terminal olefins

The divergent synthesis of syn-1,2-aminoalcohol or syn-1,2-diamine precursors from a common terminal olefin has been accomplished using a combination of palladium(II) catalysis with Lewis acid cocatalysis. Palladium(II)/bis-sulfoxide catalysis with a silver triflate cocatalyst leads for the first time to anti-2-aminooxazolines (C-O) in good to excellent yields. Simple removal of the bis-sulfoxide ligand from this reaction results in a complete switch in reactivity to afford anti-imidazolidinone products (C-N) in good yields and excellent diastereoselectivities. Mechanistic studies suggest the divergent C-O versus C-N reactivity from a common ambident nucleophile arises due to a switch in mechanism from allylic C-H cleavage/functionalization to olefin isomerization/oxidative amination.

Synthesis of the tetracyclic core (ABCE rings) of daphenylline

A concise synthesis of the tetracyclic core (ABCE rings) of daphenylline has been accomplished involving a benzobicyclo[3.3.1] lactam as the key intermediate. This bridged bicyclic intermediate was efficiently constructed via a Bronsted acid promoted intramolecular Friedel-Crafts type Michael addition of a δ-benzyl α,β-unsaturated δ-lactam.