Sequence dependence of methylation rate enhancement in meta-phenyleneethynylene foldamers.
The methylation rates of a meta-phenyleneethynylene (mPE) oligomer with a terminally-attached 4-dimethylaminopyridine (DMAP) residue are reported for a series of linear and branched methyl sulfonates; these data show that selective methylation is enhanced by locating the DMAP unit at the midpoint of the sequence, allowing the foldamer cavity to function as a reactive sieve.
Smaldone
Ronald A
RA
Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, IL 61801, USA.
Moore
Jeffrey S
JS
D015761:4-Aminopyridine / Q000031:analogs & derivatives / Q000737:chemistry; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D008745:Methylation; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000480:Alkynes; D004987:Ethers; D011108:Polymers; C436384:phenyleneethynylene; D015761:4-Aminopyridine; C003885:4-dimethylaminopyridine