Ring opening of a resin-bound chiral aziridine with phenol nucleophiles
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Ring opening of a resin-bound chiral aziridine with phenol nucleophiles. / Ottesen, Lars Korsgaard; Jaroszewski, Jerzy W; Franzyk, Henrik.
In: Journal of Organic Chemistry, Vol. 75, No. 15, 2010, p. 4983-4991.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Ring opening of a resin-bound chiral aziridine with phenol nucleophiles
AU - Ottesen, Lars Korsgaard
AU - Jaroszewski, Jerzy W
AU - Franzyk, Henrik
PY - 2010
Y1 - 2010
N2 - An efficient and versatile solid-phase route for the preparation of aryl-alkyl ethers is described. Regioselective ring opening of a resin-bound chiral aziridine with phenolic nucleophiles constitutes the key feature of the present protocol that allows incorporation of fluorescent moieties and subsequent on-resin protecting group interconversion. Initial experiments demonstrated that a competing oligomerization may occur by concomitant attacks of transient nosylamide anions on neighboring aziridines, resulting in formation of dimeric and trimeric byproduct. Expectedly, the significance of this alternative reaction pathway was strongly dependent on resin loading, and a low loading (<0.4 mmol g(-1)) was required for obtaining high yields of the desired aryl-alkyl ethers. The developed methodology allowed preparation of novel N-Fmoc-protected coumaryl amino acid building blocks, which were incorporated into peptides by solid-phase peptide synthesis.
AB - An efficient and versatile solid-phase route for the preparation of aryl-alkyl ethers is described. Regioselective ring opening of a resin-bound chiral aziridine with phenolic nucleophiles constitutes the key feature of the present protocol that allows incorporation of fluorescent moieties and subsequent on-resin protecting group interconversion. Initial experiments demonstrated that a competing oligomerization may occur by concomitant attacks of transient nosylamide anions on neighboring aziridines, resulting in formation of dimeric and trimeric byproduct. Expectedly, the significance of this alternative reaction pathway was strongly dependent on resin loading, and a low loading (<0.4 mmol g(-1)) was required for obtaining high yields of the desired aryl-alkyl ethers. The developed methodology allowed preparation of novel N-Fmoc-protected coumaryl amino acid building blocks, which were incorporated into peptides by solid-phase peptide synthesis.
KW - Former Faculty of Pharmaceutical Sciences
U2 - 10.1021/jo100505c
DO - 10.1021/jo100505c
M3 - Journal article
C2 - 20617832
VL - 75
SP - 4983
EP - 4991
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 15
ER -
ID: 21512934