Journal
ORGANIC LETTERS
Volume 24, Issue 43, Pages 8031-8035Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03262
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Funding
- National Key R&D Program of China
- National Natural Science Foundation of China
- Science and Technology Commission of Shanghai Municipality
- [2021YFA1500100]
- [21821002]
- [22031012]
- [21520780100]
- [22JC1401103]
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A Pd-catalyzed intermolecular allylic dearomatization reaction was developed for substituted beta-naphthol derivatives with Boc-protected Morita-Baylis-Hillman adducts. The reaction exhibited high yields and enantioselectivity under mild conditions, making it synthetically useful.
Pd-catalyzed intermolecular asymmetric allylic dearomatization of substituted beta-naphthol derivatives with Boc-protected Morita-Baylis-Hillman (MBH) adducts was developed. The reaction occurs smoothly in 1,4-dioxane at room temperature in the presence of [Pd(C3H5)Cl](2) (2.5 mol %), (S, S-p)-PHOX ligand (5.5 mol %), and Li2CO3 (1.0 equiv). A series of dearomatized products were afforded in moderate to excellent yields and enantioselectivity (up to 99% yield, 97% ee). Furthermore, the compatibility with gram-scale reaction and mild conditions make the current method synthetically useful.
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