Stereocontrolled Construction of 1-Vinylindanes via Intramolecular Cyclization of o-Cinnamyl Chalcones

被引：4
|
作者：
Hsueh, Nein-Chen [1 ]
Lai, Kai-Shang [1 ]
Chang, Meng-Yang [1 ,2 ]
机构：
[1] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 807, Taiwan
[2] Kaohsiung Med Univ Hosp, Dept Med Res, Kaohsiung 807, Taiwan
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 18期
关键词：
CASCADE REACTIONS; CYCLOADDITION; ACID; ALKENES; ISOMERIZATION; REDUCTION; ARYLATION; ALCOHOLS; INDENES;
D O I：
10.1021/acs.joc.8b01729
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In this paper, a concise route for the synthesis of 1-vinylindanes is described, including (i) NaBH4-mediated reduction of o-cinnamyl chalcones and (ii) sequential BF3 center dot OEt2-mediated intramolecular annulation of the resulting alkenols. The plausible mechanism is proposed and discussed herein. This protocol provides highly effective stereocontrolled cinnamyl-enone cross-coupling to construct three contiguous trans-trans stereocenters and one (E)-configured alkenyl or styryl group.
引用
收藏
页码：11415 / 11424
页数：10
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