Direct AlCl₃-catalyzed transformation of benzyl THP ethers and allyl benzyl ethers

Abstract

THP and allyl groups are frequently used for the protection of alcohols. In this study, novel direct transformations of benzyl THP ethers and allyl benzyl ethers, protected forms of alcohols, are reported. TMSN₃ and AlCl₃ were employed as key azide reagent and catalyst to perform direct conversion of benzyl THP ethers and allyl benzyl ethers to azido compounds. In addition, direct nucleophile additions of carbon nucleophiles to benzyl THP ethers and allyl benzyl ethers were successfully accomplished in the presence of catalytic AlCl₃. The results indicate that this novel method could be applied to various direct transformations of benzyl THP ethers and allyl benzyl ethers such as azidation, allylation, and alkynylation.

Graphical Abstract

Keywords:

• Allyl ethers
• Aluminum(III) chloride
• catalysts
• DPM azides
• THP ethers

Disclosure statement

There are no conflicts to declare.

Additional information

Funding

This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education [2018R1D1A1B07047572].