Complete reversal in Wacker oxidation of acetonides and cyclic carbonates of allylic diols
Conference
·
OSTI ID:250088
- Sung Kyun Kwan Univ., Suwon (Korea, Republic of); and others
The palladium(II)-catalyzed oxidation of terminal olefins to give methyl ketones (Wacker prossess) is well established in organic synthetic reactions. However palladium(II)-catalyzed oxidation of acetonide or cyclic carbonate of terminal allylic diol afforded aldehyde or {alpha},{beta}-unsaturated aldehyde as the sole products, resulting of anti-Markovnikov hydration. Alternatively, for the internal olefins of the substituted allylic diols, (E)-allylic diol provided {beta}-keto-product, whereas (Z)-allylic diol afforded {alpha}-keto-product. The acetonides and cyclic carbonates of the substituted allylic diols yielded {beta}-keto-products and {alpha},{beta}-unsaturated ketones.
- OSTI ID:
- 250088
- Report Number(s):
- CONF-9508100--
- Country of Publication:
- United States
- Language:
- English
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