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Sodium Perborate—A Convenient Baeyer–Villiger Oxidation Reagent in the Synthesis of the Corey Aldehyde
Author(s) -
Espiritu Maria,
Handley Paul N.,
Neumann Ralf
Publication year - 2003
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200390032
Subject(s) - sodium perborate , chemistry , reagent , tetrahydrate , regioselectivity , baeyer–villiger oxidation , aldehyde , peracetic acid , formic acid , organic chemistry , yield (engineering) , hydrogen peroxide , catalysis , materials science , crystal structure , metallurgy
Sodium perborate tetrahydrate is a cheap, safe and readily available alternative to the commonly used peracetic acid for the Baeyer–Villiger oxidation step of the Corey aldehyde synthesis. Chloroketo acid 1 is smoothly converted by sodium perborate tetrahydrate in formic acid to the chloroketolactone 2 in 66% isolated yield. In contrast to previously reported reactions using other oxidants, the formation of the lactone is completely regioselective in favour of the “bridgehead‐migrated” isomer 2 .