Facile Synthesis of Azaspirocycles via Iron Trichloride-Promoted Cyclization/Chlorination of Cyclic 8-Aryl-5-aza-5-tosyl-2-en-7-yn-1-ols
摘要:
A simple and efficient FeCl3-promoted cyclization/chlorination of cyclic tosylamine-tethered 8-aryl-2-en-7-yn-1-ols was observed. The reaction proceeded instantaneously at 23 degrees C in air to afford (Z)-4-(arylchloromethylene)-substituted azaspirocycles in good to excellent yields. This transformation can also be applied to the synthesis of spirocarbocyclic analogues from cyclic 8-aryl-2-en-7-yn-1-ols and FeCl3.
Facile Synthesis of Azaspirocycles via Iron Trichloride-Promoted Cyclization/Chlorination of Cyclic 8-Aryl-5-aza-5-tosyl-2-en-7-yn-1-ols
摘要:
A simple and efficient FeCl3-promoted cyclization/chlorination of cyclic tosylamine-tethered 8-aryl-2-en-7-yn-1-ols was observed. The reaction proceeded instantaneously at 23 degrees C in air to afford (Z)-4-(arylchloromethylene)-substituted azaspirocycles in good to excellent yields. This transformation can also be applied to the synthesis of spirocarbocyclic analogues from cyclic 8-aryl-2-en-7-yn-1-ols and FeCl3.
Facile Synthesis of Spirocyclic Ketones via Gold(I)-Catalyzed Claisen-Type Rearrangement of Cyclic 8-Aryl-2,7-enyn-1-ols
作者:Ming-Chang P. Yeh、Hui-Fen Pai、Chuen-Yo Hsiow、Yan-Rong Wang
DOI:10.1021/om900833k
日期:2010.1.11
The gold(I)-catalyzed Claisen-type rearrangement of cyclic 8-aryl-2,7-enyn-1-ols proceeds via a cationic allylic vinyl ethergold intermediate to give spirocyclic ketones. The reaction proceeded via attack of the hydroxyl group onto the gold-activated alkynes followed by [3,3]-sigmatropic rearrangement to generate the spirocyclic ketones. This transformation can be applied to the synthesis of aza-