Efficient and versatile COMU-mediated solid-phase submonomer synthesis of arylopeptoids (oligomeric N-substituted aminomethyl benzamides)

TY - JOUR

T1 - Efficient and versatile COMU-mediated solid-phase submonomer synthesis of arylopeptoids (oligomeric N-substituted aminomethyl benzamides)

AU - Hjelmgaard, Thomas

AU - Faure, Sophie

AU - Stærk, Dan

AU - Taillefumier, Claude

AU - Nielsen, John

PY - 2011/10/7

Y1 - 2011/10/7

N2 - The development of a highly efficient methodology for solid-phase synthesis of para- and meta-arylopeptoids (oligomeric N-substituted aminomethyl benzamides) with free acids or free amides at the C-terminus is described. The arylopeptoids were synthesised by means of a convenient submonomer protocol in which the arylopeptoid residues were created in an iterative manner on the growing chain using an acylation-substitution cycle. The uronium salt COMU was found to be the most efficient reagent for ensuring fast and clean couplings of the benzoic acid building blocks.

AB - The development of a highly efficient methodology for solid-phase synthesis of para- and meta-arylopeptoids (oligomeric N-substituted aminomethyl benzamides) with free acids or free amides at the C-terminus is described. The arylopeptoids were synthesised by means of a convenient submonomer protocol in which the arylopeptoid residues were created in an iterative manner on the growing chain using an acylation-substitution cycle. The uronium salt COMU was found to be the most efficient reagent for ensuring fast and clean couplings of the benzoic acid building blocks.

U2 - 10.1039/c1ob05729d

DO - 10.1039/c1ob05729d

M3 - Journal article

C2 - 21837337

SN - 1477-0520

VL - 9

SP - 6832

EP - 6843

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

ER -