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

✍ Scribed by Guibourdenche, Christel ;Podlech, Joachim ;Seebach, Dieter

• Book ID: 102905108
• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 1012 KB
• Volume: 1996
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199619960710

✦ Synopsis

Abstract

The diazo ketones derived from Z‐ and Boc‐protected alanine, valine, and alanyl‐alanine (1–5) were decomposed by catalytic amounts of silver benzoate/Et~3~N 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.