Method and catalyst for synthesising aziridine
AssigneeUniversity of East Anglia
InventorsSean Patrick Bew, Sean Michael Thurston, Paolo Pesce
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Abstract
The present invention relates to methods of synthesising aziridines including isotopically labelled aziridines, said methods comprising contacting an imine or one or more precursors thereof with a diazo compound in the presence of a phosphoramide or a phosphoramide-derived catalyst. The present invention also relates to aziridines, modified aziridines and aziridine-derived compounds preparable by the aforementioned methods, and to phosphoramide or phosphoramide-derived catalysts suitable for use in such methods.
Claims21
1-38. (canceled)
A method of synthesising aziridine (III) or a salt thereof, said method comprising contacting imine (I), or a salt or one or more precursors thereof, with a diazo compound (II) or a salt thereof in the presence of a catalyst:
- wherein R1, R2, R3, R4 and R5 each independently represent any atom or group, and wherein the catalyst is a compound of formula (IV) or a salt thereof, or a compound of formula (V) or a salt thereof:
- wherein X is O, S or NR9, and R6, R7, R8 and R9 each independently represent any atom or group.
An isotopically labelled aziridine or a salt thereof, wherein the isotopically labelled aziridine is not a meso compound, but would be a meso compound if it were not isotopically labelled.
A compound of formula (IV) or a salt thereof, or a compound of formula (V) or a salt thereof:
- wherein X is O, S or NR9, and R6, R7, R8 and R9 each independently represent any atom or group, with the proviso that when X is O, R6 is —SO2CF3, and R7 and R8 together form a chiral bidentate ligand of formula (VIb):
- wherein Y6 and Y7 are the same and are selected from hydrogen,
- the compound is not a compound of formula (IV) or a salt thereof.
A compound of formula (IV) or a salt thereof, or a compound of formula (V) or a salt thereof:
- wherein X is O, S or NR9, and R6, R7, R8 and R9 each independently represent any atom or group, and wherein the compound is attached to a solid support.
Dependencies are inferred from the claim text.