Enamines from the biomass derivative Cyrene and reactions with isocyanates and ketenes

Harald Podversnik; Ian Curtis; Elsie Pieterse; Martyn Jevric; Christopher J Sumby; Ben W Greatrex

doi:10.1016/j.tetlet.2023.154755

Enamines from the biomass derivative Cyrene and reactions with isocyanates and ketenes

Harald Podversnik
, Ian Curtis
, Elsie Pieterse
, Martyn Jevric
, Christopher J Sumby
, Ben W Greatrex

Faculty of Science, Ag, Business and Law

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

8 Citations (Scopus)

Abstract

To extend the chemical space accessible from the biomass-derived platform chemical Cyrene, enamines have been prepared and their reactions with selected electrophiles have been examined. The crystalline enamines prepared from morpholine (89% yield) and piperidine (79% yield) were stable and showed excellent reactivity with isocyanates, isothiocyanates and ketenes to give amides, thioamides or cyclobutanones, respectively.

Original language	English
Article number	154755
Journal	Tetrahedron Letters
Volume	129
DOIs	https://doi.org/10.1016/j.tetlet.2023.154755
Publication status	Published - 6 Oct 2023

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https://hdl.handle.net/1959.11/58814

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title = "Enamines from the biomass derivative Cyrene and reactions with isocyanates and ketenes",

abstract = "To extend the chemical space accessible from the biomass-derived platform chemical Cyrene, enamines have been prepared and their reactions with selected electrophiles have been examined. The crystalline enamines prepared from morpholine (89\% yield) and piperidine (79\% yield) were stable and showed excellent reactivity with isocyanates, isothiocyanates and ketenes to give amides, thioamides or cyclobutanones, respectively.",

author = "Harald Podversnik and Ian Curtis and Elsie Pieterse and Martyn Jevric and Sumby, \{Christopher J\} and \{W Greatrex\}, Ben",

year = "2023",

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journal = "Tetrahedron Letters",

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T1 - Enamines from the biomass derivative Cyrene and reactions with isocyanates and ketenes

AU - Podversnik, Harald

AU - Curtis, Ian

AU - Pieterse, Elsie

AU - Jevric, Martyn

AU - Sumby, Christopher J

AU - W Greatrex, Ben

PY - 2023/10/6

Y1 - 2023/10/6

N2 - To extend the chemical space accessible from the biomass-derived platform chemical Cyrene, enamines have been prepared and their reactions with selected electrophiles have been examined. The crystalline enamines prepared from morpholine (89% yield) and piperidine (79% yield) were stable and showed excellent reactivity with isocyanates, isothiocyanates and ketenes to give amides, thioamides or cyclobutanones, respectively.

AB - To extend the chemical space accessible from the biomass-derived platform chemical Cyrene, enamines have been prepared and their reactions with selected electrophiles have been examined. The crystalline enamines prepared from morpholine (89% yield) and piperidine (79% yield) were stable and showed excellent reactivity with isocyanates, isothiocyanates and ketenes to give amides, thioamides or cyclobutanones, respectively.

U2 - 10.1016/j.tetlet.2023.154755

DO - 10.1016/j.tetlet.2023.154755

M3 - Article

SN - 0040-4039

VL - 129

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 154755

ER -

Enamines from the biomass derivative Cyrene and reactions with isocyanates and ketenes

Abstract

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