Gold-Catalyzed Tandem Intramolecular Heterocyclization/Petasis-Ferrier Rearrangement of 2-(Prop-2-ynyloxy)benzaldehydes as an Expedient Route to Benzo[b]oxepin-3(2H)-ones

被引：60

作者：

Sze, Ella Min Ling ^{[1
]}

Rao, Weidong ^{[1
]}

Koh, Ming Joo ^{[1
]}

Chan, Philip Wai Hong ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 05期

关键词：

aldehydes; cyclization; gold; homogeneous catalysis; steric hindrance; CARBONYL-COMPOUNDS; COUPLING REACTION; PTERULINIC ACID; CYCLIZATION; ALKYNES; CARBOCYCLIZATION; METATHESIS; CYCLOISOMERIZATION; 1-BENZOXEPINES; DERIVATIVES;

D O I：

10.1002/chem.201003096

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The golden ring: A synthetic approach to benzo[b]oxepin-3(2a H)-ones by heterocyclization/Petasis-Ferrier rearrangement of 2-(prop-2-ynyloxy) benzaldehydes is reported. Uniquely, the ring formation was found to only proceed efficiently in the presence of a gold catalyst. Substitution at the position ortho to the ethereal group on the salicylaldehyde ring was shown to dramatically enhance reactivity (see graphic). © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1437 / 1441

页数：5

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