钯（0）催化的取代β-萘酚与森田-贝利斯-希尔曼（MBH）加合物的分子间不对称烯丙基脱芳构化反应
Palladium(0)-Catalyzed Intermolecular Asymmetric Allylic Dearomatization of Substituted β-Naphthols with Morita-Baylis-Hillman (MBH) Adducts.
作者信息
Zhang Qing-Xia, Gu Qing, You Shu-Li
机构信息
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
出版信息
Org Lett. 2022 Nov 4;24(43):8031-8035. doi: 10.1021/acs.orglett.2c03262. Epub 2022 Oct 20.
Pd-catalyzed intermolecular asymmetric allylic dearomatization of substituted β-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(CH)Cl] (2.5 mol %), (, )-PHOX ligand (5.5 mol %), and LiCO (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.
开发了钯催化的取代β-萘酚衍生物与Boc保护的森田-贝利斯-希尔曼（MBH）加合物的分子间不对称烯丙基去芳构化反应。该反应在室温下于1,4-二氧六环中，在[Pd(CH)Cl]（2.5 mol%）、（, ）-PHOX配体（5.5 mol%）和LiCO（1.0当量）存在下顺利进行。得到了一系列去芳构化产物，产率中等至优异，对映选择性高达（产率99%，对映体过量97%）。此外，该方法与克级反应的兼容性以及温和的条件使其在合成上具有实用性。
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