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 journalArticlepeer-review

35 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
DOIs
Publication statusPublished - May 1 1991

ASJC Scopus subject areas

  • Organic Chemistry

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