Improved solid-phase synthesis and study of arylopeptoids with conformation-directing side chains

TY - JOUR

T1 - Improved solid-phase synthesis and study of arylopeptoids with conformation-directing side chains

AU - Hjelmgaard, Thomas

AU - Faure, Sophie

AU - De Santis, Emiliana

AU - Stærk, Dan

AU - Alexander, Bruce D.

AU - Edwards, Alison A.

AU - Taillefumier, Claude

AU - Nielsen, John

PY - 2012/6/10

Y1 - 2012/6/10

N2 - The development of an improved methodology for iterative solid-phase synthesis of para- and meta-arylopeptoids (oligomeric N-substituted aminomethyl benzamides) using benzoyl chloride building blocks is described. This methodology has enabled the synthesis of arylopeptoids with tert-butyl and phenyl side chains, which allows for complete control over the amide conformation: the tert-butyl results in a 100% cis amide conformation while the phenyl side chain results in a 100% trans amide conformation. The method has furthermore enabled the first synthesis and preliminary conformational studies of arylopeptoids bearing (S)-N-(1-phenylethyl) side chains.

AB - The development of an improved methodology for iterative solid-phase synthesis of para- and meta-arylopeptoids (oligomeric N-substituted aminomethyl benzamides) using benzoyl chloride building blocks is described. This methodology has enabled the synthesis of arylopeptoids with tert-butyl and phenyl side chains, which allows for complete control over the amide conformation: the tert-butyl results in a 100% cis amide conformation while the phenyl side chain results in a 100% trans amide conformation. The method has furthermore enabled the first synthesis and preliminary conformational studies of arylopeptoids bearing (S)-N-(1-phenylethyl) side chains.

U2 - 10.1016/j.tet.2011.12.049

DO - 10.1016/j.tet.2011.12.049

M3 - Journal article

SN - 0040-4020

VL - 68

SP - 4444

EP - 4454

JO - Tetrahedron

JF - Tetrahedron

IS - 23

ER -