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Easy access to β-halo amino esters and aziridine 2-carboxylic esters from halohydrins

✍ Scribed by Saı̈d Boukhris; Abdelaziz Souizi

Book ID
104253436
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
96 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

The halohydrins prepared from epoxide esters, were treated with hydroxylamine derivatives. In subsequent reaction with NaOH/K 2 CO 3 /Bu 4 NHSO 4 the N-protected b-halo a-aminoesters thus obtained were converted into N-hydroxy ariridine 2-carboxylic esters in good yields.

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N-Substituted a-amino 13-oxo esters have been obtained by amination of 13-enamino esters with ethyl N-[(4-nitrobenzenesuiphonyl)oxy]carbamate (NsONHCOzEt), in the absence of added bases. The use of optically active pvrrolldines with (72 symmetry as ehiral auxiliaries induces diastereoselectivities u