39998-99-7

Upstream product

• 56772-63-5 (R)-octan-2-yl methanesulfonate 
• 139-02-6 sodium phenoxide 
• 34817-25-9 (S)-1-methylheptyl tosylate 
• 135683-65-7 (1S)-1-methylheptyl N,N’-dicyclohexylcarbamimidate 
• 108-95-2 phenol 
• 6169-06-8 (S)-2-Octanol 
• 462-06-6 fluorobenzene 
• 5978-70-1 (R)-Octan-2-ol 
• 111-66-0 oct-1-ene 

Downstream Products

• 3004-93-1 (R)-(-)-2-methyloctanoic acid 
• 3004-93-1 (2S)-2-Methyl-octanoic acid 

Relevant academic research and scientific papers

Iridium-catalyzed, intermolecular hydroetherification of unactivated aliphatic alkenes with phenols

Metal-catalyzed addition of an O-H bond to an alkene is a desirable process because it allows for rapid access to ethers from abundant starting materials without the formation of waste, without rearrangements, and with the possibility to control the stereoselectivity. We report the intermolecular, metal-catalyzed addition of phenols to unactivated α-olefins. Mechanistic studies of this rare catalytic reaction revealed a dynamic mixture of resting states that undergo O-H bond oxidative addition and subsequent olefin insertion to form ether products.

Design and asymmetric synthesis of chiral diaryliodonium salts

The application of chiral hypervalent iodine reagents in asymmetric synthesis is highly desirable, as the reagents are metal-free, environmentally benign and employed under mild conditions. Three chiral diaryliodonium salts have been designed to provide chemoselectivity and asymmetric induction in asymmetric α-phenylation of carbonyl compounds. The synthetic routes to the selected targets are detailed herein, together with a structural investigation into the diastereoselectivity of the alkylation process.

Inversion of configuration of alcohols with O-alkyl-N,N'-dicyclohexylisoureas

(S)-(+)-N,N'-Dicyclohexyl-O-(1-methylheptyl)isourea [(S)-2] reacts with acetic acid in cyclohexane to give (R)-(-)-(1-methylheptyl) acetate [(R)-3] with 100% inversion of configuration. Reaction of isourea (R)-2 with phenol proceeds also with inversion of configuration (99.8%) yielding (S)-(+)-(1-methylheptyl) phenyl ether [(S)-4] as the main product; optically active 2- and 4-(1-methylheptyl)phenols [(S)-5] and [(S)-6], respectively, are formed simultaneously. These byproducts, besides others resulting from hydride-shifts, document that the mechanism proceeds via the methylheptyl cation intermediate.