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:61
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
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
收藏
页码:1437 / 1441
页数:5
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