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Stereoselective Shono Oxidations: Use of Alkylidene Protective Groups (Supporting Information)

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posted on 2023-10-05, 01:22 authored by Shinnosuke AKAHANE, Haruka MORIZUMI, Yoshikazu KITANO, Yohei OKADA

Anodic formation of N,O-acetals using amides or carbamates as starting materials, commonly referred to as Shono oxidation, has been an iconic reaction in the field of synthetic organic electrochemistry. However, it is, in principle, not stereoselective and the commonly used neighboring-carbonyl-group participation is not usually effective. Herein, we demonstrate that the use of alkylidene protective groups is extremely effective in controlling the stereoselectivity. Although the detailed mechanism remains an open question, under our reaction conditions, the conformation restriction effect is dominant rather than the steric hindrance effect.

Funding

Establishment of systematic synthesis method for next-generation medium-molecular-weight drugs

Japan Society for the Promotion of Science

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Japan Society for the Promotion of Science

TEPCO Memorial Foundation

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Corresponding author email address

yokada@cc.tuat.ac.jp

Copyright

© 2023 The Author(s).

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