Highly efficient solid-phase oxidative cleavage of olefins by OsO 4-NaIO4 in the intramolecular N-acyliminium Pictet-Spengler reaction

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Standard

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

Harvard

Nielsen, TE & Meldal, M 2005, 'Highly efficient solid-phase oxidative cleavage of olefins by OsO 4-NaIO4 in the intramolecular N-acyliminium Pictet-Spengler reaction', Organic Letters, bind 7, nr. 13, s. 2695-2698. https://doi.org/10.1021/ol050870r

APA

Nielsen, T. E., & Meldal, M. (2005). Highly efficient solid-phase oxidative cleavage of olefins by OsO 4-NaIO4 in the intramolecular N-acyliminium Pictet-Spengler reaction. Organic Letters, 7(13), 2695-2698. https://doi.org/10.1021/ol050870r

Vancouver

Nielsen TE, Meldal M. Highly efficient solid-phase oxidative cleavage of olefins by OsO 4-NaIO4 in the intramolecular N-acyliminium Pictet-Spengler reaction. Organic Letters. 2005;7(13):2695-2698. https://doi.org/10.1021/ol050870r

Author

Nielsen, Thomas E. ; Meldal, Morten. / Highly efficient solid-phase oxidative cleavage of olefins by OsO 4-NaIO4 in the intramolecular N-acyliminium Pictet-Spengler reaction. I: Organic Letters. 2005 ; Bind 7, Nr. 13. s. 2695-2698.

Bibtex

@article{cb0bf7c2ebfe49d8a9e30ce4a1c84aa2,
title = "Highly efficient solid-phase oxidative cleavage of olefins by OsO 4-NaIO4 in the intramolecular N-acyliminium Pictet-Spengler reaction",
abstract = "(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.",
author = "Nielsen, {Thomas E.} and Morten Meldal",
year = "2005",
doi = "10.1021/ol050870r",
language = "English",
volume = "7",
pages = "2695--2698",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "13",

}

RIS

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