13133-99-8

Upstream product

• 1391824-34-2 5-methyl-4-phenyl-3,6-dihydro-2H-pyran 
• 309270-97-1 (Z)-4-methyl-3-phenyl-2-penten-1-ol 
• 309270-99-3 (E)-4-methyl-3-phenyl-2-penten-1-ol 
• 13133-96-5 4-hydroxy-4-methyl-3-phenylpentanoic acid γ-lactone 
• 13133-97-6 2-methyl-3-phenylpentane-2,5-diol 

Relevant academic research and scientific papers

Unconventional isomerization of allylic alcohols to allylcarbinols mediated by lanthanide catalysts

We report here the catalytic isomerization of aryl-substituted allylic alcohols mediated by lanthanide alkoxide complexes. The conversion yields allylcarbinols as the products of the olefin isomerization process, but with different olefinic positions than those afforded by typical transition metal catalysts. The average isolated product yields in these reactions are 65-81%. The catalytic cycle and the source of the unusual olefinic positioning are proposed to involve a strong interaction between the Lewis acidic La 3+ ion and the substrate hydroxyl group.

Synthesis of allylic and homoallylic alcohols from unsaturated cyclic ethers using a mild and selective C-O reduction approach

Unsaturated cyclic ethers can be mildly and selectively reduced with catalytic amounts of B(C6F5)3 in the presence of an alkylsilane. The allylic position is preferentially reduced with minimal or no scrambling of olefin geometry. For electronically equivalent substrates, steric factors guide the reducing agent to the least substituted site.