Deprotection of carboxylic esters of β-lactam homologues. Cleavage of p-methoxybenzyl, diphenylmethyl, and tert-butyl esters effected by a phenolic matrix

Sigeru Torii, Hideo Tanaka, Masatoshi Taniguchi, Yutaka Kameyama, Michio Sasaoka, Takashi Shiroi, Ryo Kikuchi, Ichiro Kawahara, Akihiro Shimabayashi, Shigemitsu Nagao

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

p-Methoxybenzyl, diphenylmethyl, and tert-butyl esters were deprotected by gentle heating in phenol. This method of ester cleavage played an important role in β-lactam synthesis. The mechanism of the reaction is believed to involve a proton relay through a hydrogen-bonded phenolic matrix.

Original languageEnglish
Pages (from-to)3633-3637
Number of pages5
JournalJournal of Organic Chemistry
Volume56
Issue number11
Publication statusPublished - 1991

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Deprotection of carboxylic esters of β-lactam homologues. Cleavage of p-methoxybenzyl, diphenylmethyl, and tert-butyl esters effected by a phenolic matrix'. Together they form a unique fingerprint.

  • Cite this

    Torii, S., Tanaka, H., Taniguchi, M., Kameyama, Y., Sasaoka, M., Shiroi, T., Kikuchi, R., Kawahara, I., Shimabayashi, A., & Nagao, S. (1991). Deprotection of carboxylic esters of β-lactam homologues. Cleavage of p-methoxybenzyl, diphenylmethyl, and tert-butyl esters effected by a phenolic matrix. Journal of Organic Chemistry, 56(11), 3633-3637.