Palladium-Catalyzed Enyne Cyclization towards Complex Cyclopentanes

Significance

The use of directing groups in synthesis allows for complex materials to be prepared with higher regio-, diastereo- and/or enantioselectivity than usually to be expected. Cárdenas and co-workers have shown that enynes can be cyclized using a palladium catalyst and a diboron reagent (J. Am. Chem. Soc. 2007, 129, 1874). In this communication, the authors utilize this protocol on homopropargyl alcohols, showing that complex cyclopentanes can be prepared with ­excellent diastereoselectivity.