A New Alternative for the Synthesis of Highly Functionalized Phosphoryl Derivatives

Abstract

Nucleophilic addition of diethylphosphite to Bayllis-Hillman acetate 5 in the presence of K₂CO₃ provides E and Z-allylphosphonates 6 , which could be converted in the presence of N-bromosuccinimide (NBS) and benzoyl peroxide as catalyst into allylbromides 2 . The primary one is further converted via an efficient tandem “formylation-hydrolysis” into the corresponding primary allylalcohol 8 . The secondary allylbromides 2 react with TEAF via a β -elimination to give buta-1,3-dienes 9 .

Keywords:

• Functionalyzed allyl bromides
• formylation-hydrolysis
• N-Bromosuccinimide
• phosphonates

Notes

*Determined by ¹P NMR spectral analysis.