Highly efficient solid-phase oxidative cleavage of olefins by OsO 4-NaIO4 in the intramolecular N-acyliminium Pictet-Spengler reaction
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Highly efficient solid-phase oxidative cleavage of olefins by OsO 4-NaIO4 in the intramolecular N-acyliminium Pictet-Spengler reaction. / Nielsen, Thomas E.; Meldal, Morten.
I: Organic Letters, Bind 7, Nr. 13, 2005, s. 2695-2698.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - Highly efficient solid-phase oxidative cleavage of olefins by OsO 4-NaIO4 in the intramolecular N-acyliminium Pictet-Spengler reaction
AU - Nielsen, Thomas E.
AU - Meldal, Morten
PY - 2005
Y1 - 2005
N2 - (Chemical Equation Presented) In the present investigation, solid-supported peptide olefins were converted quantitatively to aldehydes via the OsO 4-NaIO4-mediated oxidative cleavage reaction. Addition of DABCO was essential to efficiently suppress the formation of hydroxymethyl ketone side products. The generated aldehydes were used in intramolecular N-acyliminium Pictet-Spengler reactions to produce highly pure pyrroloisoquinoline derivatives. The methodology was extended to allylglycine derivatives to enable the incorporation of pyrroloisoquinoline scaffolds within peptides.
AB - (Chemical Equation Presented) In the present investigation, solid-supported peptide olefins were converted quantitatively to aldehydes via the OsO 4-NaIO4-mediated oxidative cleavage reaction. Addition of DABCO was essential to efficiently suppress the formation of hydroxymethyl ketone side products. The generated aldehydes were used in intramolecular N-acyliminium Pictet-Spengler reactions to produce highly pure pyrroloisoquinoline derivatives. The methodology was extended to allylglycine derivatives to enable the incorporation of pyrroloisoquinoline scaffolds within peptides.
UR - http://www.scopus.com/inward/record.url?scp=26844432234&partnerID=8YFLogxK
U2 - 10.1021/ol050870r
DO - 10.1021/ol050870r
M3 - Journal article
C2 - 15957924
AN - SCOPUS:26844432234
VL - 7
SP - 2695
EP - 2698
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 13
ER -
ID: 326846971