Synthesis of mono-O-alkylated homooxacalix[3]arene and a protection–deprotection strategy for homooxacalix[3]arene

Wu, Chong; Ikejiri, Yusuke; Zeng, Xi; Elsegood, Mark R.J.; Redshaw, Carl; Yamato, Takehiko

Abstract

The regioselective synthesis of mono-O-alkylated homooxacalix[3]arene is accomplished for the first time. The synthetic route relies on two key steps: (i) a facile protection of two OH groups at the lower rim of the homooxacalix[3]arene and (ii) the deprotection of 9- anthrylmethyl groups via the Pd/C-catalyzed hydrogenation under atmospheric hydrogen. An efficient protection- deprotection strategy for the functionalization of homooxacalix[ 3]arene is presented.

Citation

Wu, C., Ikejiri, Y., Zeng, X., Elsegood, M. R., Redshaw, C., & Yamato, T. (2017). Synthesis of mono-O-alkylated homooxacalix[3]arene and a protection–deprotection strategy for homooxacalix[3]arene. Organic Letters, 19(1), 66-69. https://doi.org/10.1021/acs.orglett.6b03338

• Acceptance Date: Dec 10, 2016
• Online Publication Date: Dec 12, 2016
• Publication Date: 2017-02
• Deposit Date: Dec 13, 2016
• Publicly Available Date: Dec 14, 2017
• Journal: Organic letters
• Print ISSN: 1523-7060
• Electronic ISSN: 1523-7052
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 19
• Issue: 1
• Pages: 66-69
• DOI: https://doi.org/10.1021/acs.orglett.6b03338
• Keywords: Mono-O-alkylated homooxacalix[3]arene; Homooxacalix[3]arene
• Public URL: https://hull-repository.worktribe.com/output/472183
• Publisher URL: http://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b03338
• Additional Information: This is a description of an article which has been published in: Organic letters, 2017, v.19, issue 1.