157968-87-1

Upstream product

• 20425-48-3 methyl (R)-(+)-citronellate 
• 157921-41-0 (R)-7-tert-butyldimethylsilyloxy-2,4-dimethyl-2-heptanol 
• 157921-42-1 (R)-1-tert-butyldimethylsilyloxy-4,6-dimethyl-5-heptene 
• 1617-32-9 (E)-3-pentenoic acid 
• 76-26-6 camphor-10-sulfonic acid 
• 157921-46-5 (4R,5R)-6-bromo-4,6-dimethyl-5-heptanolide 
• 157921-40-9 methyl (R)-6-tert-butyldimethylsilyloxy-3-methylhexanoate 
• 20425-49-4 methyl (R)-3-methyl-6-hydroxyhexanoate 
• 157921-45-4 (R)-4,6-dimethyl-5-heptenoic acid 
• 141243-76-7 (R)-4,6-dimethyl-5-hepten-1-ol 

Downstream Products

• 206123-70-8 (3S,5R,6S)-3,5-dimethyl-6-isopropyl-3,4,5,6-tetrahydropyran-2-one 
• 206123-70-8 (2R,4R,5S)-2,4,6-trimethyl-5-heptanolide 

Relevant academic research and scientific papers

Highly Stereoselective 2-Oxonia-Cope Rearrangement: A Platform Enabling At-Will Control of Regio-, Enantio-, and Diastereoselectivity in the Vinylogous Aldol Reactions of Aldehydes

A distinctly different approach for the vinylogous aldolation of aldehydes is described, which exploits 2-oxonia-Cope rearrangement reactions between two readily available partners, a set of rationally designed chiral homoallylic alcohol synthons and aldehydes, under simple conditions. In these processes, chirality transfer from the former to the latter is nearly perfect, giving rise to excellent enantio- and diastereoselectivity without the regioselectivity issue associated with traditional vinylogous aldol reactions.

Synthesis of (2S,4R,5S)-2,4,6-Trimethyl-5-heptanolide, a Sex Pheromone Component for Macrocentrus grandii

(2S,4R,5S)-2,4,6-Trimethyl-5-heptanolide (1), a sex pheromone component for Macrocentrus grandii, was synthesized by starting from methyl (R)-citronellate (2) and employing bromolactonization (10 -> 11) as the key reaction.