87761-90-8

Upstream product

• 5703-57-1 3-phenylpent-4-enoic acid 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 104-54-1 3-Phenylpropenol 

Downstream Products

• 25359-49-3 Methyl 4-oxo-3-phenylpentanoate 
• 92927-63-4 (4R^*, 5S^*)-dihydro-5-methyl-4-phenyl-2(3H)-furanone 
• 950838-18-3 (4S,5R)-5-(hydroxymethyl)-4-phenyldihydrofuran-2(3H)-one 
• 1423026-43-0 (R)-methyl 3-((S)-oxiran-2-yl)-3-phenylpropanoate 
• 112423-41-3 cis-5-Methyl-4-phenyl-4,5-dihydro-2(3H)-furanone 
• 112654-28-1 2-Allyl-2-[2-((2S,3R)-5-oxo-3-phenyl-tetrahydro-furan-2-yl)-1-phenyl-ethyl]-malononitrile 
• 23725-23-7 5-methyl-4-phenyloxolane-2-one 
• 131323-50-7 trans-β-Phenyl-γ-hydroxy-δ-valerolactone 
• 131323-50-7 cis-β-Phenyl-γ-hydroxy-δ-valerolactone 

Relevant academic research and scientific papers

Optically pure γ-butyrolactones and epoxy esters via two stereocentered HKR of 3-substituted epoxy esters: A formal synthesis of (-)-paroxetine, Ro 67-8867 and (+)-eldanolide

The HKR of racemic anti- or syn-3-substituted epoxy esters catalyzed by a Co(iii)salen complex provides ready access to the corresponding enantioenriched 3,4-disubstituted γ-butyrolactones and 3-substituted epoxy esters. This strategy has been successfully employed in the formal synthesis of biologically active 3,4-disubstituted piperidine derivatives, (-)-paroxetine and Ro 67-8867 and a natural product, (+)-eldanolide.

Lactones 30. Reaction of halolactones with trialkylphosphites

The reaction of halolactones with trialkylphosphites in the presence of water afforded dehalogenated lactones.

Stereocontrolled iodolactonization of acyclic olefinic amides

Acyclic olefinic amides were iodolactonized in the mixed solvent of CH3CN and H2O (90:10, v/v) under reflux to give products with trans configuration of the newly formed iodomethyl to the inherent alkyl group in high yield.

Synthesis of 4-Penten-4-olides (γ-Methylene-γ-butyrolactones) via 4-Pentenoic Acids

4-Penten-4-olides (γ-Methylene-γ-butyrolactones) 7 are easily accessible starting from allylic alcohols 1, which on ortho ester Claisen rearrangement and hydrolytic work-up furnish 4-pentenoic acids 5.The latter on iodolactonization and hydrogen iodide elimination by means of 1,8-diazabicycloundec-7-ene (DBU) furnish 7, in good over-all yield and with variable substitution patterns. - Iodolactonization under kinetic control shows moderate 1,2- or 1,3-asymmetric induction (3:1 and ca. 2:1, respectively).The composition of the iodolactone mixtures 6 as well as the individual relative configurations are deduced from 1H and 13C NMR data. - Similary, the spirobipentenolide 13 is obtained starting from diethyl diallylmalonate (9) via 11 resulting from ester iodocyclization.