Organic letters

Practical asymmetric approach to medium-sized carbocycles based on the combination of two Ru-catalyzed transformations and a Lewis acid-induced cyclization

F López, L Castedo, JL Mascareñas

文献索引：Lopez, Fernando; Castedo, Luis; Mascarenas, Jose L. Organic Letters, 2005 , vol. 7, # 2 p. 287 - 290

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被引用次数: 24

摘要

Ruthenium-catalyzed coupling of allyl ethyl ether to optically active 1-trimethylsilyl-1-alkyn-3- ols, followed by in situ ketalization and Lewis-acid-induced cyclization, affords enantiomerically pure 1, 5-oxygen-bridged eight-and nine-membered carbocycles. Opening of the oxygen bridge under basic or electron transfer conditions provides optically pure medium-sized carbocycles, products that are difficult to construct using other currently ...