53979-32-1

Upstream product

• 100884-47-7 allyl-(4-methoxy-benzyl)-malonic acid 
• 1929-29-9 3-(4-methoxyphenyl)propanoic acid 
• 106-95-6 allyl bromide 
• 591-80-0 pent-4-enoic acid 
• 2746-25-0 p-Methoxybenzyl bromide 
• 6335-37-1 2-(4-methoxybenzyl)malonic acid diethyl ester 
• 824-94-2 p-methoxybenzyl chloride 
• 101892-24-4 allyl-(4-methoxy-benzyl)-malonic acid diethyl ester 
• 2049-80-1 (2-propenyl)propanedioic acid diethyl ester 

Downstream Products

• 858021-82-6 6-methoxy-4-methyl-1,2,3,4-tetrahydro-[2]naphthoic acid 
• 1448804-70-3 C₁₉H₂₁N₃O₆S 
• 4255-32-7 1-(4-Methoxy-benzyl)-buten-⁽³⁾-ylamin 
• 1448804-69-0 (±)-tert-butyl (1-(4-methoxyphenyl)pent-4-en-2-yl)carbamate 

Relevant academic research and scientific papers

N -Boc amines to oxazolidinones via Pd(II)/bis-sulfoxide/br?nsted acid Co-catalyzed allylic C-H oxidation

A Pd(II)/bis-sulfoxide/Br?nsted acid catalyzed allylic C-H oxidation reaction for the synthesis of oxazolidinones from simple N-Boc amines is reported. A range of oxazolidinones are furnished in good yields (avg 63%) and excellent diastereoselectivities (avg 15:1) to furnish products regioisomeric from those previously obtained using allylic C-H amination reactions. Mechanistic studies suggest the role of the phosphoric acid is to furnish a Pd(II)bis-sulfoxide phosphate catalyst that promotes allylic C-H cleavage and π-allylPd functionalization with a weak, aprotic oxygen nucleophile and to assist in catalyst regeneration.

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.

SAR of 2-benzyl-4-aminopiperidines NK1 antagonists. Part 2. Synthesis of CGP 49823

CGP 49823 is a potent NK1 antagonist which is centrally active after oral administration. The SAR of the C-2 substituent was investigated with respect to the affinity to the NK1 receptor. A practical synthesis of CGP 49823, suitable for scale-up, was developed. The key-step, a tandem acyliminium ion cyclization/Ritter reaction, gave trans-2-benzyl-4-acetamido-piperidines with high diastereoselectivity.