Structural analysis and reactivity of unusual tetrahedral intermediates enabled by SmI2-mediated reduction of barbituric acids: vinylogous N-acyliminium additions to α-hydroxy-N-acyl-carbamides

Michal Szostak; Brice Sautier; David J. Procter

doi:10.1039/c3cc48932a

Structural analysis and reactivity of unusual tetrahedral intermediates enabled by SmI₂-mediated reduction of barbituric acids: vinylogous N-acyliminium additions to α-hydroxy-N-acyl-carbamides

Michal Szostak, Brice Sautier, David J. Procter

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

Structural characterisation and reactivity of new tetrahedral intermediates based on a highly modular barbituric acid scaffold, formed via chemoselective electron transfer using the SmI₂–H₂O reagent, are reported. Lewis acid promoted cleavage of bicyclic α-amino alcohols affords vinylogous N-acyliminium ions, which undergo selective (>95 : 5, 1,4 over 1,2) capture with a suite of diverse nucleophiles in a practical sequence to biologically active uracil derivatives.

Original language	English (US)
Pages (from-to)	2518-2521
Number of pages	4
Journal	Chemical Communications
Volume	50
Issue number	19
DOIs	https://doi.org/10.1039/c3cc48932a
State	Published - Feb 7 2014
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c3cc48932a

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abstract = "Structural characterisation and reactivity of new tetrahedral intermediates based on a highly modular barbituric acid scaffold, formed via chemoselective electron transfer using the SmI2–H2O reagent, are reported. Lewis acid promoted cleavage of bicyclic α-amino alcohols affords vinylogous N-acyliminium ions, which undergo selective (>95 : 5, 1,4 over 1,2) capture with a suite of diverse nucleophiles in a practical sequence to biologically active uracil derivatives.",

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Structural analysis and reactivity of unusual tetrahedral intermediates enabled by SmI₂-mediated reduction of barbituric acids: vinylogous N-acyliminium additions to α-hydroxy-N-acyl-carbamides. / Szostak, Michal; Sautier, Brice; Procter, David J.
In: Chemical Communications, Vol. 50, No. 19, 07.02.2014, p. 2518-2521.

Research output: Contribution to journal › Article › peer-review

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AU - Sautier, Brice

AU - Procter, David J.

PY - 2014/2/7

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AB - Structural characterisation and reactivity of new tetrahedral intermediates based on a highly modular barbituric acid scaffold, formed via chemoselective electron transfer using the SmI2–H2O reagent, are reported. Lewis acid promoted cleavage of bicyclic α-amino alcohols affords vinylogous N-acyliminium ions, which undergo selective (>95 : 5, 1,4 over 1,2) capture with a suite of diverse nucleophiles in a practical sequence to biologically active uracil derivatives.

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Structural analysis and reactivity of unusual tetrahedral intermediates enabled by SmI₂-mediated reduction of barbituric acids: vinylogous N-acyliminium additions to α-hydroxy-N-acyl-carbamides

Abstract

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