Acid- and base-stable esters: A new protecting group for carboxylic acids

Michio Kurosu; Kallolmay Biswas; Prabagaran Narayanasamy; Dean C. Crick

doi:10.1055/s-2007-983801

Acid- and base-stable esters: A new protecting group for carboxylic acids

Michio Kurosu, Kallolmay Biswas, Prabagaran Narayanasamy, Dean C. Crick

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

An acid- and base-stable protecting group for carboxylic acids is described. The esters of (2,6-dichloro-4-methoxyphenyl)(2,4-dichlorophenyl) methanol are stable to Bransted and Lewis acids, Brønsted bases, and a wide variety of nucleophiles; however, the esters can be conveniently deprotected by a solvolytic displacement reaction with 20% trifluoroacetic acid.

Original language	English (US)
Pages (from-to)	2513-2516
Number of pages	4
Journal	Synthesis
Issue number	16
DOIs	https://doi.org/10.1055/s-2007-983801
State	Published - Aug 16 2007
Externally published	Yes

Keywords

Acid-stable ester
Base-stable ester
Carboxylic acid protecting group
Chlorodiphenylmethyl esters

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-2007-983801

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title = "Acid- and base-stable esters: A new protecting group for carboxylic acids",

abstract = "An acid- and base-stable protecting group for carboxylic acids is described. The esters of (2,6-dichloro-4-methoxyphenyl)(2,4-dichlorophenyl) methanol are stable to Bransted and Lewis acids, Br{\o}nsted bases, and a wide variety of nucleophiles; however, the esters can be conveniently deprotected by a solvolytic displacement reaction with 20% trifluoroacetic acid.",

keywords = "Acid-stable ester, Base-stable ester, Carboxylic acid protecting group, Chlorodiphenylmethyl esters",

author = "Michio Kurosu and Kallolmay Biswas and Prabagaran Narayanasamy and Crick, {Dean C.}",

year = "2007",

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day = "16",

doi = "10.1055/s-2007-983801",

language = "English (US)",

pages = "2513--2516",

journal = "Synthesis (Germany)",

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TY - JOUR

T1 - Acid- and base-stable esters

T2 - A new protecting group for carboxylic acids

AU - Kurosu, Michio

AU - Biswas, Kallolmay

AU - Narayanasamy, Prabagaran

AU - Crick, Dean C.

PY - 2007/8/16

Y1 - 2007/8/16

N2 - An acid- and base-stable protecting group for carboxylic acids is described. The esters of (2,6-dichloro-4-methoxyphenyl)(2,4-dichlorophenyl) methanol are stable to Bransted and Lewis acids, Brønsted bases, and a wide variety of nucleophiles; however, the esters can be conveniently deprotected by a solvolytic displacement reaction with 20% trifluoroacetic acid.

AB - An acid- and base-stable protecting group for carboxylic acids is described. The esters of (2,6-dichloro-4-methoxyphenyl)(2,4-dichlorophenyl) methanol are stable to Bransted and Lewis acids, Brønsted bases, and a wide variety of nucleophiles; however, the esters can be conveniently deprotected by a solvolytic displacement reaction with 20% trifluoroacetic acid.

KW - Acid-stable ester

KW - Base-stable ester

KW - Carboxylic acid protecting group

KW - Chlorodiphenylmethyl esters

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DO - 10.1055/s-2007-983801

M3 - Article

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EP - 2516

JO - Synthesis (Germany)

JF - Synthesis (Germany)

SN - 0039-7881

IS - 16

ER -

Acid- and base-stable esters: A new protecting group for carboxylic acids

Abstract

Keywords

ASJC Scopus subject areas

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