Solid-phase synthesis of structurally diverse heterocycles by an amide-ketone condensation/N-acyliminium pictet-spengler sequence

Research output: Contribution to journalJournal articlepeer-review

Standard

Solid-phase synthesis of structurally diverse heterocycles by an amide-ketone condensation/N-acyliminium pictet-spengler sequence. / Komnatnyy, Vitaly V.; Givskov, Michael; Nielsen, Thomas E.

In: Chemistry. A European Journal, Vol. 18, No. 52, 12.2012, p. 16793-16800.

Research output: Contribution to journalJournal articlepeer-review

Harvard

Komnatnyy, VV, Givskov, M & Nielsen, TE 2012, 'Solid-phase synthesis of structurally diverse heterocycles by an amide-ketone condensation/N-acyliminium pictet-spengler sequence', Chemistry. A European Journal, vol. 18, no. 52, pp. 16793-16800. https://doi.org/10.1002/chem.201202745

APA

Komnatnyy, V. V., Givskov, M., & Nielsen, T. E. (2012). Solid-phase synthesis of structurally diverse heterocycles by an amide-ketone condensation/N-acyliminium pictet-spengler sequence. Chemistry. A European Journal, 18(52), 16793-16800. https://doi.org/10.1002/chem.201202745

Vancouver

Komnatnyy VV, Givskov M, Nielsen TE. Solid-phase synthesis of structurally diverse heterocycles by an amide-ketone condensation/N-acyliminium pictet-spengler sequence. Chemistry. A European Journal. 2012 Dec;18(52):16793-16800. https://doi.org/10.1002/chem.201202745

Author

Komnatnyy, Vitaly V. ; Givskov, Michael ; Nielsen, Thomas E. / Solid-phase synthesis of structurally diverse heterocycles by an amide-ketone condensation/N-acyliminium pictet-spengler sequence. In: Chemistry. A European Journal. 2012 ; Vol. 18, No. 52. pp. 16793-16800.

Bibtex

@article{3d13369210c342b4a521443b0e5db056,
title = "Solid-phase synthesis of structurally diverse heterocycles by an amide-ketone condensation/N-acyliminium pictet-spengler sequence",
abstract = "An efficient approach for the solid-phase synthesis of structurally diverse heterocyclic compounds is presented. Under acidic reaction conditions, peptidic levulinamides undergo intramolecular ketone-amide condensation reactions to form cyclic N-acyliminium intermediates. In the presence of a tethered nucleophile, a second cyclization reaction results in the formation of a fused bicyclic ring system. The scope of the methodology was demonstrated by several combinations of substituted ketones and nucleophiles, the latter conveniently originating from amino acids with functionalized side chains, such as tryptophan, substituted phenylalanines, and cysteine. The cyclization sequence provides diastereomerically pure products in high yields. In one extension of the methodology, the resulting relative stereochemistry of the products enables the formation of bridged ring systems by a unique cyclative release mechanism.",
author = "Komnatnyy, {Vitaly V.} and Michael Givskov and Nielsen, {Thomas E}",
note = "Copyright {\textcopyright} 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",
year = "2012",
month = dec,
doi = "10.1002/chem.201202745",
language = "English",
volume = "18",
pages = "16793--16800",
journal = "Chemistry: A European Journal",
issn = "0947-6539",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "52",

}

RIS

TY - JOUR

T1 - Solid-phase synthesis of structurally diverse heterocycles by an amide-ketone condensation/N-acyliminium pictet-spengler sequence

AU - Komnatnyy, Vitaly V.

AU - Givskov, Michael

AU - Nielsen, Thomas E

N1 - Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

PY - 2012/12

Y1 - 2012/12

N2 - An efficient approach for the solid-phase synthesis of structurally diverse heterocyclic compounds is presented. Under acidic reaction conditions, peptidic levulinamides undergo intramolecular ketone-amide condensation reactions to form cyclic N-acyliminium intermediates. In the presence of a tethered nucleophile, a second cyclization reaction results in the formation of a fused bicyclic ring system. The scope of the methodology was demonstrated by several combinations of substituted ketones and nucleophiles, the latter conveniently originating from amino acids with functionalized side chains, such as tryptophan, substituted phenylalanines, and cysteine. The cyclization sequence provides diastereomerically pure products in high yields. In one extension of the methodology, the resulting relative stereochemistry of the products enables the formation of bridged ring systems by a unique cyclative release mechanism.

AB - An efficient approach for the solid-phase synthesis of structurally diverse heterocyclic compounds is presented. Under acidic reaction conditions, peptidic levulinamides undergo intramolecular ketone-amide condensation reactions to form cyclic N-acyliminium intermediates. In the presence of a tethered nucleophile, a second cyclization reaction results in the formation of a fused bicyclic ring system. The scope of the methodology was demonstrated by several combinations of substituted ketones and nucleophiles, the latter conveniently originating from amino acids with functionalized side chains, such as tryptophan, substituted phenylalanines, and cysteine. The cyclization sequence provides diastereomerically pure products in high yields. In one extension of the methodology, the resulting relative stereochemistry of the products enables the formation of bridged ring systems by a unique cyclative release mechanism.

U2 - 10.1002/chem.201202745

DO - 10.1002/chem.201202745

M3 - Journal article

C2 - 23132763

VL - 18

SP - 16793

EP - 16800

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

SN - 0947-6539

IS - 52

ER -

ID: 44311084