What question did this study set out to answer?

To evaluate sodium perborate tetrahydrate as a safer, inexpensive alternative to peracetic acid in the Baeyer–Villiger oxidation step of Corey aldehyde synthesis.

March 1, 2003Advanced Synthesis & Catalysis

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

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Authors

MEMaria EspirituCSIRO Manufacturing PHPaul HandleyQueen Mary University of London RNRalf NeumannAlbert Einstein College of Medicine

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Implication

Chemical synthesis evaluation demonstrates efficient, regioselective Baeyer–Villiger oxidation of chloroketo acid using sodium perborate, indicating a safer route to the Corey aldehyde.

Key Points

To evaluate sodium perborate tetrahydrate as a safer, inexpensive alternative to peracetic acid in the Baeyer–Villiger oxidation step of Corey aldehyde synthesis.
Treated chloroketo acid 1 with sodium perborate tetrahydrate in formic acid.
Assessed isolated yield and product regioselectivity for the resulting chloroketolactone.
Sodium perborate tetrahydrate successfully converted chloroketo acid 1 into chloroketolactone 2 in a 66% isolated yield.
The oxidation displayed complete regioselectivity in favor of the bridgehead-migrated isomer 2, contrasting with outcomes observed using other oxidants.

Cite This Study

Espiritu et al. (2003) studied this question.

synapsesocial.com/papers/6aa7660ef08b9ee964c50d22 https://doi.org/10.1002/adsc.200390032

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Implication

Chemical synthesis evaluation demonstrates efficient, regioselective Baeyer–Villiger oxidation of chloroketo acid using sodium perborate, indicating a safer route to the Corey aldehyde.

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

Discussion

Member takes

Implication

Key Points

Cite This Study

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

Discussion

Member takes

Implication

Key Points

Cite This Study

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