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

32 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

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Lactams
Esters
Phenol
Protons
Hydrogen
Heating

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Torii, S., Tanaka, H., Taniguchi, M., Kameyama, Y., Sasaoka, M., Shiroi, T., ... 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.

Deprotection of carboxylic esters of β-lactam homologues. Cleavage of p-methoxybenzyl, diphenylmethyl, and tert-butyl esters effected by a phenolic matrix. / Torii, Sigeru; Tanaka, Hideo; Taniguchi, Masatoshi; Kameyama, Yutaka; Sasaoka, Michio; Shiroi, Takashi; Kikuchi, Ryo; Kawahara, Ichiro; Shimabayashi, Akihiro; Nagao, Shigemitsu.

In: Journal of Organic Chemistry, Vol. 56, No. 11, 1991, p. 3633-3637.

Research output: Contribution to journalArticle

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, vol. 56, no. 11, pp. 3633-3637.
Torii, Sigeru ; Tanaka, Hideo ; Taniguchi, Masatoshi ; Kameyama, Yutaka ; Sasaoka, Michio ; Shiroi, Takashi ; Kikuchi, Ryo ; Kawahara, Ichiro ; Shimabayashi, Akihiro ; Nagao, Shigemitsu. / Deprotection of carboxylic esters of β-lactam homologues. Cleavage of p-methoxybenzyl, diphenylmethyl, and tert-butyl esters effected by a phenolic matrix. In: Journal of Organic Chemistry. 1991 ; Vol. 56, No. 11. pp. 3633-3637.
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