133589-22-7

Upstream product

• 133589-20-5 trans-1-phenyl-2-(tributylstannyl)epoxyethane 
• 67-64-1 acetone 
• 57132-28-2 (E)-2-methyl-4-phenylbut-3-en-2-ol 
• 133589-20-5 tri-n-butyl(cis-epoxystyryl)tin 
• 1896-62-4 (E)-benzalacetone 

Relevant academic research and scientific papers

Selective Aerobic Oxygenation of Tertiary Allylic Alcohols with Molecular Oxygen

Aerobic epoxidation of tertiary allylic alcohols remains a significant challenge. Reported here is an efficient and highly chemoselective copper-catalyzed epoxidation and semipinacol rearrangement reaction of tertiary allylic alcohols with molecular oxygen. The solvent 1,4-dioxane activates dioxygen, thereby precluding the addition of a sacrificial reductant.

Oxiranyllithium reagents: Generation from organotin precursors, addition to aldehydes and ketones, and dimerization to α,α′-dialkoxyolefins

Oxiranyllithium compounds can be generated from organotin precursors by tin-lithium exchange with butyllithium in THF at -90°C. In the presence of TMEDA, they react with aldehydes and ketones to give epoxy alcohols in good yields. In the absence of TMEDA, they dimerize to α,α′-dialkoxyolefins.

Enantioselective epoxidation of tertiary allylic alcohols by chiral dihydroperoxides

gem-Dihydroperoxides were successfully used for the enantioselective epoxidation of tertiary and primary allylic alcohols. Epoxides derived from tertiary alcohols were obtained in yields up to 71% with ee's up to 52%.