Bifunctionalized allenes. Part XXII. Coinage metal-catalyzed cycloisomerization of phosphorylated 3-(α- or β-hydroxyalkyl)allenes to 2-phosphoryl-2,5-dihydrofurans or 2-phosphoryl-5,6-dihydro-2H-pyrans

Abstract

The present paper discusses the coinage metal-catalyzed cycloisomerization reaction of phosphorylated 3-(α- or β-hydroxyalkyl)allenes. 3-(α- or β-Hydroxyalkyl)-allenylphosphonates and -allenyl phosphine oxides were smoothly converted into the 2-phosphoryl-2,5-dihydrofurans or 2-phosphoryl-5,6-dihydro-2Н-pyrans by using 5 mol % of coinage metal salts as catalyst in 5-endo-trig or 6-endo-trig cycloisomerization, respectively. Experimental conditions such as the type of the solvent, the reaction temperature, the mol % and the type of the catalyst and its influence on the yields and the reaction time of the cycloisomerization reaction of the phosphorylated 3-(α- or β-hydroxyalkyl)allenes were optimized.

GRAPHICAL ABSTRACT

Keywords:

• Cycloisomerization
• phosphorylated 3-(α- or β-hydroxyalkyl)allenes
• 2-phosphoryl-2,5-dihydrofurans
• 2-phosphoryl-5,6-dihydro-2H-pyrans
• reaction conditions

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was supported by the the Research Fund of the Konstantin Preslavsky University of Shumen under Grants No. RD-08-98/2017 and RD-08-158/2018.