Highly Chemo- and Regioselective Construction of Spirocarbocycles by a Pd(0)-Catalyzed Dearomatization of Phenol-Based Biaryls with 1,3-Dienes.
Highly Chemo- and Regioselective Construction of Spirocarbocycles by a Pd(0)-Catalyzed Dearomatization of Phenol-Based Biaryls with 1,3-Dienes.
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DOI：
10.1021/acs.orglett.6b00710
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发表时间：
2016-04
期刊：
影响因子：
5.2
通讯作者：
Lei Luo;Huayu Zheng;Jingjing Liu;Hui Wang;Yaoyu Wang;X. Luan
中科院分区：
文献类型：
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作者：
Lei Luo;Huayu Zheng;Jingjing Liu;Hui Wang;Yaoyu Wang;X. Luan
通过一系列 C-I 键氧化加成、区域选择性烯烃插入和烯丙基脱芳构化，实现了一种新型 Pd(0) 催化的苯酚衍生联芳基与 1,3-二烯的分子间碳环化。该方法以良好的收率提供了一系列具有吸引力的带有两个连续叔/季碳中心的螺环化合物，并具有优异的化学选择性和区域选择性。此外，初步结果表明，使用手性配体对该过程的不对称控制是可行的。
A novel Pd(0)-catalyzed intermolecular carbocyclization of phenol-derived biaryls with 1,3-dienes has been implemented through a sequence of oxidative addition to the C-I bond, regioselective olefin insertion, and allylative dearomatization. This method provides a broad range of attractive spirocyclic compounds bearing two contiguous tertiary/quaternary carbon centers in good yields with excellent chemoselectivity and regioselectivity. Moreover, preliminary results indicate that asymmetric control of this process is feasible with chiral ligands.