Ruiz Nerea, Vicario Jose L, Badía Dolores, Carrillo Luisa, Alonso Beatriz
Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea, Bilbao, Spain.
Org Lett. 2008 Jun 19;10(12):2613-6. doi: 10.1021/ol800934r. Epub 2008 May 20.
We have studied the ability of an alpha-imino glyoxylamide derived from (S, S)-(+)-pseudoephedrine as a valuable chiral electrophile for the preparation of alpha-amino carbonyl compounds. In this context, the addition of Grignard reagents to the azomethine moiety of this chiral electrophile afforded the expected alpha-amino amide adducts in good yields and diastereoselectivities. Moreover, these adducts have been transformed into enantioenriched alpha-amino ketones by exploiting the ability of pseudoephedrine amides to undergo selective monoaddition to the carbamoyl group with organolithium reagents.
我们研究了一种由（S，S）-（+）-伪麻黄碱衍生的α-亚氨基乙二酰胺作为制备α-氨基羰基化合物的重要手性亲电试剂的能力。在这种情况下，格氏试剂加成到手性亲电试剂的偶氮甲碱部分，以良好的产率和非对映选择性得到了预期的α-氨基酰胺加合物。此外，通过利用伪麻黄碱酰胺与有机锂试剂对氨基甲酰基进行选择性单加成的能力，这些加合物已被转化为对映体富集的α-氨基酮。
