Selective Acylations of Multifunctional Nucleophiles, Including Carbohydrates and Nucleosides, with Intermediates Generated by Wolff Rearrangement of Amino Acid Derived Diazo Ketones: Preparation of β‐Amino Acid Derivatives
1996; Wiley; Volume: 1996; Issue: 7 Linguagem: Inglês
10.1002/jlac.199619960710
ISSN0947-3440
AutoresChristel Guibourdenche, Joachim Podlech, Dieter Seebàch,
Tópico(s)Asymmetric Hydrogenation and Catalysis
ResumoThe diazo ketones derived from Z- and Boc-protected alanine, valine, and alanyl-alanine (1–5) were decomposed by catalytic amounts of silver benzoate/Et3N in the presence of polyfunctional nucleophiles such as 3-methyl-1,3-butanediol, 2-aminoethanol, carbohydrates (xylofuranose and sucrose) and nucleosides (thymidine, adenosine derivatives). In many cases, products of β-amino acylations are formed (6–14, 15b, 17–19, 21, 23, 24) with surprising functional group selectivities. The scope and limitations of the method are described.
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