1448804-70-3

Upstream product

• 5769-16-4 4-nitrobenzenesulfonyl isocyanate 
• 4255-32-7 1-(4-Methoxy-benzyl)-buten-⁽³⁾-ylamin 
• 2746-25-0 p-Methoxybenzyl bromide 
• 1448804-69-0 (±)-tert-butyl (1-(4-methoxyphenyl)pent-4-en-2-yl)carbamate 
• 53979-32-1 2-(4-methoxy-benzyl)-pent-4-enoic acid 
• 6325-93-5 p-nitrobenzenesulfonamide 

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.