Diastereoselective allylic rearrangement of Morita–Baylis–Hillman C-adducts: a facile access to functionalized 1, 2-dihydroisoquinolines

A facile protocol to construct β-selective allylic 1, 2-dihydroisoquinoline with high E/Z selectivity from its γ-regioisomer through an unexpected Lewis base or thermo-initiated rearrangement is described. This rearrangement transformation proceeds under mild reaction conditions with efficiency and...

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Bibliographic Details
Published in:Tetrahedron 2015-02, Vol.71 (6), p.941-948
Main Authors: Xu, Qiu-Qin, Qin, Tian-You, Wang, Ting-Ting, Wang, Tai-Jing, Liao, Wei-Wei
Format: Article
Language:English
Subjects:
Diastereoselectivity
Dihydroisoquinoline
Rearrangement
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Summary:A facile protocol to construct β-selective allylic 1, 2-dihydroisoquinoline with high E/Z selectivity from its γ-regioisomer through an unexpected Lewis base or thermo-initiated rearrangement is described. This rearrangement transformation proceeds under mild reaction conditions with efficiency and atom economy. The control experiments demonstrated that these rearrangement processes initiated by different modes followed two distinct mechanisms. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.12.073