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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
Author(s) -
Guibourdenche Christel,
Podlech Joachim,
Seebach Dieter
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960710
Subject(s) - chemistry , wolff rearrangement , diazo , nucleophile , amino acid , organic chemistry , catalysis , stereochemistry , biochemistry
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.