Fragment-oriented synthesis: β-elaboration of cyclic amine fragments using enecarbamates as platform intermediates

Alexandre F Trindade; Emily L Faulkner; Andrew G Leach; Adam Nelson; Stephen P Marsden

doi:10.1039/d0cc03934a

Fragment-oriented synthesis: β-elaboration of cyclic amine fragments using enecarbamates as platform intermediates

Alexandre F Trindade, Emily L Faulkner, Andrew G Leach, Adam Nelson, Stephen P Marsden

Pharmacy

University of Leeds

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

Abstract

A strategy for the β-sp3 functionalisation of cyclic amines is described. Regioselective conversion of protected amines to enecarbamates is achieved through electrochemical oxidation; these intermediates can be derivatised by functionalised alkyl halides under photoredox catalysis. The potential of the methods is highlighted by direct growth of a DCP2B-binding fragment.

Original language	English
Journal	Chemical communications (Cambridge, England)
DOIs	https://doi.org/10.1039/d0cc03934a
Publication status	Published - 6 Jul 2020

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title = "Fragment-oriented synthesis: β-elaboration of cyclic amine fragments using enecarbamates as platform intermediates",

abstract = "A strategy for the β-sp3 functionalisation of cyclic amines is described. Regioselective conversion of protected amines to enecarbamates is achieved through electrochemical oxidation; these intermediates can be derivatised by functionalised alkyl halides under photoredox catalysis. The potential of the methods is highlighted by direct growth of a DCP2B-binding fragment.",

author = "Trindade, {Alexandre F} and Faulkner, {Emily L} and Leach, {Andrew G} and Adam Nelson and Marsden, {Stephen P}",

year = "2020",

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doi = "10.1039/d0cc03934a",

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journal = "Chemical communications (Cambridge, England)",

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AU - Trindade, Alexandre F

AU - Faulkner, Emily L

AU - Leach, Andrew G

AU - Nelson, Adam

AU - Marsden, Stephen P

PY - 2020/7/6

Y1 - 2020/7/6

N2 - A strategy for the β-sp3 functionalisation of cyclic amines is described. Regioselective conversion of protected amines to enecarbamates is achieved through electrochemical oxidation; these intermediates can be derivatised by functionalised alkyl halides under photoredox catalysis. The potential of the methods is highlighted by direct growth of a DCP2B-binding fragment.

AB - A strategy for the β-sp3 functionalisation of cyclic amines is described. Regioselective conversion of protected amines to enecarbamates is achieved through electrochemical oxidation; these intermediates can be derivatised by functionalised alkyl halides under photoredox catalysis. The potential of the methods is highlighted by direct growth of a DCP2B-binding fragment.

U2 - 10.1039/d0cc03934a

DO - 10.1039/d0cc03934a

M3 - Article

C2 - 32626868

SN - 1359-7345

JO - Chemical communications (Cambridge, England)

JF - Chemical communications (Cambridge, England)

ER -

Fragment-oriented synthesis: β-elaboration of cyclic amine fragments using enecarbamates as platform intermediates

Abstract

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