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1,1,1,3,3,3-Hexafluoroisopropanol: A Recyclable Organocatalyst for N-Boc Protection of Amines

Akbar Heydari*, Samad Khaksar, Mahmood Tajbakhsh

*Chemistry Department, Tarbiat Modares University, P.O. Box 14115-175, Tehran 18716, Iran, Email:

A. Heydari, S. Khaksar, M. Tajbakhsh, Synthesis, 2008, 3126-3130.

DOI: 10.1055/s-2008-1067272


The use of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as solvent and catalyst allows a simple and efficient, chemoselective mono-N-Boc protection of various structurally diverse amines with di-tert-butyl dicarbonate. The catalyst can be readily recycled. No competitive side reactions such as formation of isocyanates, ureas, and oxazolidinones from α-amino alcohols were observed.

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Key Words

amines, Boc anhydride, Boc-protected amines, chemoselectivity, HFIP, organocatalysis, hydrogen bonding

ID: J66-Y2008-2740