The silicon-directed Nazarov cyclization was shown to proceed with good to excellent stereoselectivity in cyclohexenyl systems bearing a variety of ring substituents. In all cases the trans family of isomers predominated, and cis ring-fused products were formed exclusively. The potential for stereocontrol by increasing the bulk of silicon substituents was limited for five-membered rings and good for six-membered rings. Phenylsilanes were ...