Convenient Formation of Diphenylmethyl Esters Using Diphenylmethyl Trichloroacetimidate

Arijit A. Adhikari; Jigisha P. Shah; Kyle T. Howard; Christopher M. Russo; Daniel R. Wallach; Matthew R. Linaburg; John D. Chisholm

doi:10.1055/s-0033-1340293

Convenient Formation of Diphenylmethyl Esters Using Diphenylmethyl Trichloroacetimidate

Arijit A. Adhikari, Jigisha P. Shah, Kyle T. Howard, Christopher M. Russo, Daniel R. Wallach, Matthew R. Linaburg, John D. Chisholm

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

21 Scopus citations

Abstract

Diphenylmethyl trichloroacetimidate is a useful reagent for the protection of carboxylic acids as their corresponding diphenylmethyl esters. These esterifications proceed rapidly without the need for an added catalyst or promoter. A variety of carboxylic acid substrates undergo esterification in excellent yields with the trichloroacetimidate reagent, including substrates possessing acid- or base-sensitive functionality. Protection of a carboxylic acid with a highly enolizable α-stereocenter using diphenylmethyl imidate was also accomplished without racemization.

Original language	English (US)
Article number	ST-2013-S0967-L
Pages (from-to)	283-287
Number of pages	5
Journal	Synlett
Volume	25
Issue number	2
DOIs	https://doi.org/10.1055/s-0033-1340293
State	Published - Jan 2014

Keywords

C-O bond formation
chemoselectivity
esterification
esters
protecting groups

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-0033-1340293

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title = "Convenient Formation of Diphenylmethyl Esters Using Diphenylmethyl Trichloroacetimidate",

abstract = "Diphenylmethyl trichloroacetimidate is a useful reagent for the protection of carboxylic acids as their corresponding diphenylmethyl esters. These esterifications proceed rapidly without the need for an added catalyst or promoter. A variety of carboxylic acid substrates undergo esterification in excellent yields with the trichloroacetimidate reagent, including substrates possessing acid- or base-sensitive functionality. Protection of a carboxylic acid with a highly enolizable α-stereocenter using diphenylmethyl imidate was also accomplished without racemization.",

keywords = "C-O bond formation, chemoselectivity, esterification, esters, protecting groups",

author = "Adhikari, {Arijit A.} and Shah, {Jigisha P.} and Howard, {Kyle T.} and Russo, {Christopher M.} and Wallach, {Daniel R.} and Linaburg, {Matthew R.} and Chisholm, {John D.}",

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T1 - Convenient Formation of Diphenylmethyl Esters Using Diphenylmethyl Trichloroacetimidate

AU - Adhikari, Arijit A.

AU - Shah, Jigisha P.

AU - Howard, Kyle T.

AU - Russo, Christopher M.

AU - Wallach, Daniel R.

AU - Linaburg, Matthew R.

AU - Chisholm, John D.

PY - 2014/1

Y1 - 2014/1

N2 - Diphenylmethyl trichloroacetimidate is a useful reagent for the protection of carboxylic acids as their corresponding diphenylmethyl esters. These esterifications proceed rapidly without the need for an added catalyst or promoter. A variety of carboxylic acid substrates undergo esterification in excellent yields with the trichloroacetimidate reagent, including substrates possessing acid- or base-sensitive functionality. Protection of a carboxylic acid with a highly enolizable α-stereocenter using diphenylmethyl imidate was also accomplished without racemization.

AB - Diphenylmethyl trichloroacetimidate is a useful reagent for the protection of carboxylic acids as their corresponding diphenylmethyl esters. These esterifications proceed rapidly without the need for an added catalyst or promoter. A variety of carboxylic acid substrates undergo esterification in excellent yields with the trichloroacetimidate reagent, including substrates possessing acid- or base-sensitive functionality. Protection of a carboxylic acid with a highly enolizable α-stereocenter using diphenylmethyl imidate was also accomplished without racemization.

KW - C-O bond formation

KW - chemoselectivity

KW - esterification

KW - esters

KW - protecting groups

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Convenient Formation of Diphenylmethyl Esters Using Diphenylmethyl Trichloroacetimidate

Abstract

Keywords

ASJC Scopus subject areas

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