Stereocontrolled formation of epoxy peroxide functionality appended to a lactam ring

Area of Science:

• Organic Chemistry
• Stereoselective Synthesis
• Peroxide Chemistry

Background:

• Allylic alcohols are versatile synthetic intermediates.
• Lactam rings introduce unique structural and electronic properties.
• Epoxy alkyl peroxides are valuable synthetic building blocks.

Purpose of the Study:

• To investigate the reaction of tert-butyl hydroperoxide and tin(IV) chloride with allylic alcohols containing a lactam ring.
• To determine the stereochemical outcome and product distribution of this reaction.
• To compare the results with analogous reactions involving carbocyclic allylic alcohols.

Main Methods:

• Reaction of allylic alcohols with lactam rings using tert-butyl hydroperoxide and tin(IV) chloride.
• Diastereoselective synthesis.
• Product characterization and stereochemical analysis.

Main Results:

• The reaction predominantly yields epoxy alkyl peroxides.
• High diastereoselection was observed in the formation of these peroxides.
• The stereochemistry and products differ markedly from reactions with tert-butyl hydroperoxide-VO(acac)2.

Conclusions:

• Tin(IV) chloride promotes a highly diastereoselective epoxidation of allylic lactam alcohols.
• The presence of the lactam ring significantly influences the reaction pathway and stereochemical outcome.
• This study highlights a novel and efficient method for synthesizing complex epoxy alkyl peroxides.