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A Direct and Stereoretentive Synthesis of Amides from Cyclic Alcohols
Author(s) -
Mondal Deboprosad,
Bellucci Luca,
Lepore Salvatore D.
Publication year - 2011
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.201101165
Subject(s) - chemistry , nitrile , carbocation , nucleophile , thionyl chloride , fluoride , titanium , organic chemistry , chloride , catalysis , inorganic chemistry
Chlorosulfites prepared in situ using thionyl chloride react with nitrile complexes of titanium(IV) fluoride to give a one‐pot conversion of alcohols into amides. For the first time, amides are obtained from cyclic alcohols with stereoretention. Critical to the design of these new Ti IV reactions has been the use of little‐explored Ti IV nitrile complexes that are thought to chelate chlorosulfites in the transition state tocreate a carbocation that is rapidly captured by the nitrile nucleophile through a front‐side attack mechanism.