Sodium Perborate—A Convenient Baeyer–Villiger Oxidation Reagent in the Synthesis of the Corey Aldehyde | Zendy

Espiritu Maria | Zendy; Handley Paul N. | Zendy; Neumann Ralf | Zendy

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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 .

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