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

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(2): 283-287
DOI: 10.1055/s-0033-1340293

letter

Convenient Formation of Diphenylmethyl Esters Using Diphenylmethyl Trichloroacetimidate

Arijit A. Adhikari

Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, NY 13244, USA Fax: +1(315)4434070 eMail: jdchisho@syr.edu

,

Jigisha P. Shah

Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, NY 13244, USA Fax: +1(315)4434070 eMail: jdchisho@syr.edu

,

Kyle T. Howard

Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, NY 13244, USA Fax: +1(315)4434070 eMail: jdchisho@syr.edu

,

Christopher M. Russo

Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, NY 13244, USA Fax: +1(315)4434070 eMail: jdchisho@syr.edu

,

Daniel R. Wallach

Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, NY 13244, USA Fax: +1(315)4434070 eMail: jdchisho@syr.edu

,

Matthew R. Linaburg

Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, NY 13244, USA Fax: +1(315)4434070 eMail: jdchisho@syr.edu

,

John D. Chisholm*

Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, NY 13244, USA Fax: +1(315)4434070 eMail: jdchisho@syr.edu

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Abstract

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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.

Key words

esters - protecting groups - C–O bond formation - chemoselectivity - esterification

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Referenzen

References and Notes

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