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Bio‐Based Amides from Renewable Isosorbide by a Direct and Atom‐Economic Boric Acid Amidation Methodology
Author(s) -
Janvier Marine,
MoebsSanchez Sylvie,
Popowycz Florence
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600186
Subject(s) - chemistry , organic chemistry , boric acid , isatin , atom economy , combinatorial chemistry , isosorbide , catalysis
The functionalization of bio‐sourced isohexides has proved challenging over the last number of years, especially in polymer and medicinal chemistry. We report herein the synthesis of bio‐based amido‐isohexides by the known boric acid catalysed amidation reaction. The coupling reaction was successfully performed with aliphatic and aromatic carboxylic acids. The extension of the scope of the reaction to eight Boc‐protected amino acids is also described, the products being obtained in moderate to good yields. A preliminary screening of these new potential organocatalysts was carried out for the aldolization of isatin.