Reaction of vinyl triflates of α-keto esters with primary amines: efficient synthesis of aziridine carboxylates

Vinyl triflates of α-keto esters react smoothly with primary amines to provide aziridine carboxylates in good yields. In all cases, little or no stereoselectivity was observed. A mechanistic study has shown that aziridine carboxylates are strictly formed under kinetic control. The origin of this lac...

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Bibliographic Details
Published in:Tetrahedron 2002-10, Vol.58 (42), p.8425-8432
Main Authors: Tranchant, Marie-José, Dalla, Vincent, Jabin, Ivan, Decroix, Bernard
Format: Article
Language:English
Subjects:
aziridine carboxylates
vinyl triflates
α-keto esters
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Summary:Vinyl triflates of α-keto esters react smoothly with primary amines to provide aziridine carboxylates in good yields. In all cases, little or no stereoselectivity was observed. A mechanistic study has shown that aziridine carboxylates are strictly formed under kinetic control. The origin of this lack of stereoselectivity is explained by a non- or poorly stereoselective proton transfer. Vinyl triflates of α-keto esters react with primary amines to provide good yields of aziridine carboxylates.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)01031-1