Synthesis of spiro[4.5]cyclohexadienones with an allene motif via a base-promoted intramolecular ipso-Friedel-Crafts addition of phenols to propargyl bromides

被引：23

作者：

Nemoto, Tetsuhiro ^{[1
]}

Wu, Riliga ^{[1
]}

Zhao, Zengduo ^{[1
]}

Yokosaka, Takuya ^{[1
]}

Hamada, Yasumasa ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, Chiba 2608675, Japan

来源：

TETRAHEDRON | 2013年 / 69卷 / 16期

关键词：

Alkylation; Dearomatization; ipso-Friedel-Crafts addition; Palladium; Spiro compounds; HIGHLY REGIOSELECTIVE SYNTHESIS; ALLYLIC ALKYLATION; ENANTIOSELECTIVE CONSTRUCTION; ASYMMETRIC DEAROMATIZATION; CYCLIZATION; DERIVATIVES; CARBON; CARBAPENAM; ALLYLATION; DIENONES;

D O I：

10.1016/j.tet.2013.02.082

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We developed a novel synthetic method for allenyl spiro[4.5]cyclohexadienone derivatives based on a base-promoted intramolecular ipso-Friedel-Crafts addition of phenols to propargyl bromides. The present spirocyclization proceeded in a CH2Cl2-tert-BuOH mixed solvent system using potassium tert-butoxide as the base, and produced the corresponding spiro[4.5]cyclohexadienone derivatives with an allene motif in up to 99% yield. This-type allenyl spirocycle was also accessible through Pd-catalyzed intramolecular ipso-Friedel-Crafts alkylation when a propargyl carbonate derivative with a naphthol unit was used as a substrate. Acid-promoted skeletal rearrangement of the reaction adducts was also examined. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：3403 / 3409

页数：7

共 47 条

[1]

Appel TR, 2003, EUR J ORG CHEM, V2003, P47

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