195863-85-5

Upstream product

• 2216-51-5 (-)-menthol 
• 180477-54-7 (1S,2R,4R)-1-isopropyl-4-methyl-2-(3-methylbut-2-en-1-yloxy)cyclohexane 
• 119441-91-7 prop-1-en-2-ylzinc(II) chloride 
• 753488-83-4 (1S,2R,4R)-2-(2,3-dimethylbut-2-en-1-yloxy)-1-isopropyl-4-methylcyclohexane 

Downstream Products

• 2216-51-5 (-)-menthol 
• 78-84-2 isobutyraldehyde 
• 753488-83-4 (1S,2R,4R)-2-(2,3-dimethylbut-2-en-1-yloxy)-1-isopropyl-4-methylcyclohexane 
• 180477-54-7 (1S,2R,4R)-1-isopropyl-4-methyl-2-(3-methylbut-2-en-1-yloxy)cyclohexane 
• 2623-23-6 L-menthyl acetate 
• 136375-73-0 [[[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl]oxy]methyl]benzene 
• 76358-81-1 tert-butyl(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)dimethylsilane 
• 40940-58-7 (1S,2R,4R)-2-(allyloxy)-1-isopropyl-4-methylcyclohexane 

Relevant academic research and scientific papers

Decarboxylative alkenylation

Olefin chemistry, through pericyclic reactions, polymerizations, oxidations, or reductions, has an essential role in the manipulation of organic matter. Despite its importance, olefin synthesis still relies largely on chemistry introduced more than three decades ago, with metathesis being the most recent addition. Here we describe a simple method of accessing olefins with any substitution pattern or geometry from one of the most ubiquitous and variegated building blocks of chemistry: alkyl carboxylic acids. The activating principles used in amide-bond synthesis can therefore be used, with nickel- or iron-based catalysis, to extract carbon dioxide from a carboxylic acid and economically replace it with an organozinc-derived olefin on a molar scale. We prepare more than 60 olefins across a range of substrate classes, and the ability to simplify retrosynthetic analysis is exemplified with the preparation of 16 different natural products across 10 different families.

Allyl, methallyl, prenyl, and methylprenyl ethers as protected alcohols: Their selective cleavage with diphenyldisulfone under neutral conditions

Diphenyldisulfone is a mild and efficient reagent for selective cleavage of methylprenyl (2,3-dimethylbut-2-en-1-yl), prenyl (3-methylbut-2-en1-yl), and methallyl (2-methylallyl) ethers. These reaction conditions are compatible with the presence of other protecting groups such as acetals, acetates, and allyl, benzyl, and TBDMS ethers. Exposure of 2,3-dimethylbut-2-en-1-yl and 3-methylbut-2-en1-yl ethers to diphenyldisulfone led to the formation of 2,3-dimethylbuta-1,3-diene and isoprene, respectively. 2-Methylallyl ethers undergo isomerization to 2-methylpropenyl ethers, which are easily hydrolyzed into the corresponding free alcohols and isobutyraldehyde.