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Reactive Esters in Amide Ligation with β‐Hydroxyamines
Author(s) -
Pirrung Michael C.,
Zhang Fa,
Ambadi Sudhakar,
IbarraRivera Tannya R.
Publication year - 2012
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.201200624
Subject(s) - chemistry , racemization , amide , intramolecular force , transesterification , acylation , reagent , intermolecular force , organic chemistry , combinatorial chemistry , molecule , catalysis
Abstract Amide formation between mildly activated esters and 1,2‐amino alcohols occurs without the need for coupling reagents. The reaction pathway involves facile intermolecular transesterification and intramolecular O→N transacylation. The method is environmentally friendly and offers no risk of racemization via highly activated acylating intermediates.