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A New Method for Selective Activation of Amino, Hydroxy, and Mercapto Carboxylic Acids at the Carboxyl Group: Preparation of Thiol and Selenol Esters
Author(s) -
Gais HansJoachim,
Lied Thomas
Publication year - 1978
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197802671
Subject(s) - chemistry , enol , thiol , ketone , carboxylic acid , functional group , organic chemistry , alkali metal , amino acid , combinatorial chemistry , catalysis , biochemistry , polymer
Effective new acylating agents , the enol esters ( 3 ), are accessible by selective reaction of the ketone ( 1 ) with carboxylic acids ( 2 ) containing OH, NH 2 , or SH groups. The stable enol esters ( 3 ) (yields >90%) are transformed into thiol esters ( 4 ), XS, in good yields on reaction with alkali metal thiolates. Potential applications exist in the synthesis of macrolides and peptides.