[3,3]-Sigmatropic Rearrangement/5-exo-dig Cyclization Reactions of Benzyl Alkynyl Ethers: Synthesis of Substituted 2-Indanones and Indenes

被引：24

作者：

Tudjarian, Armen A. ^{[1
]}

Minehan, Thomas G. ^{[1
]}

机构：

[1] Calif State Univ Northridge, Dept Chem & Biochem, Northridge, CA 91330 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 09期

关键词：

ALIPHATIC CLAISEN REARRANGEMENT; ALPHA-DIAZO KETONES; ALLYL VINYL ETHERS; ACETYLENIC ETHERS;

D O I：

10.1021/jo200271s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Substituted benzyl alkynyl ethers, prepared from the corresponding alpha-alkoxy ketones in a two-step sequence involving enol triflate formation and KOtBu-induced E2 elimination, undergo [3,3] -sigmatropic rearrangement/intramolecular 5-exo-dig cyclization at 60 degrees C to form substituted 2-indanones in good overall yields. 1,3-cis-Disubstituted-2-indanones are formed preferentially when the benzylic substituent R-1 is bulky. Substituted indenes may be prepared from 2-indanones in high yields by Horner-Wadsworth-Emmons reaction.

引用

页码：3576 / 3581

页数：6

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