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Synthesis of α‐Acyloxy‐α′‐hydroxy Ketones via Cyclic Carbonate Intermediates Generated from Tertiary Bromopropargylic Alcohols and Cs 2 CO 3
Author(s) -
Shemyakina Olesya A.,
Volostnykh Ol'ga G.,
Stepanov Anton V.,
Ushakov Igor' A.
Publication year - 2019
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.201901226
Subject(s) - chemistry , reagent , tertiary alcohols , carbonate , organic chemistry , ketone , carboxylic acid , alcohol , medicinal chemistry
A facile approach towards α‐acyloxy‐α′‐hydroxy ketones by reaction of readily available tertiary bromopropargylic alcohols and carboxylic acids in system Cs 2 CO 3 /H 2 O/DMF (50–55 °C, 4 h) was developed. Key intermediates of this synthesis are cyclic carbonates generated in situ from bromopropargylic alcohols and Cs 2 CO 3 which have been utilized as both reagent and base promoter.