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Copper‐Catalyzed Aerobic CC Bond Cleavage of Lactols with N‐Hydroxy Phthalimide for Synthesis of Lactones
Author(s) -
Tnay Ya Lin,
Chiba Shunsuke
Publication year - 2015
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201403196
Subject(s) - phthalimide , radical , chemistry , enol , bond cleavage , enol ether , catalysis , medicinal chemistry , organic chemistry
The transformation of cyclic hemiacetals (lactols) into lactones has been achieved by Cu‐catalyzed aerobic CC bond cleavage in the presence of N ‐hydroxy phthalimide (NHPI). The present process is composed of a multistep sequence including a) formation of exo ‐cyclic enol ethers by dehydration; b) addition of phthalimide N ‐oxyl radical to the enol ethers followed by trapping of the resulting C‐radicals with molecular oxygen to form peroxy radicals; c) reductive generation of oxy radicals and subsequent β‐radical fragmentation to generate lactones.