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

作者：Sze Ella Min Ling; Rao Weidong; Koh Ming Joo; Chan Philip Wai Hong^*

来源：Chemistry - A European Journal, 2011, 17(5): 1437-1441.

DOI：10.1002/chem.201003096

• aldehydes
• cyclization
• gold
• homogeneous catalysis
• steric hindrance

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).

• 出版日期2011
• 单位南阳理工学院