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

Autor:	Qiuqin Xu, Ting-Ting Wang, Tian-You Qin, Wei-Wei Liao, Tai-Jing Wang
Rok vydání:	2015
Předmět:	Reaction conditions Allylic rearrangement Stereochemistry Chemistry Atom economy Organic Chemistry Drug Discovery Lewis acids and bases Selectivity Biochemistry Adduct
Zdroj:	Tetrahedron. 71:941-948
ISSN:	0040-4020
DOI:	10.1016/j.tet.2014.12.073
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::64e2e968d0f38a8efadb4955aeb6d82c https://doi.org/10.1016/j.tet.2014.12.073 Zobrazit plný text záznamu Full Text from ScienceDirect