Abstract
A regio‐ and stereoselective three‐component coupling reaction generates functionalized (Z)‐silyl enol ethers through a vinylation/[1,2]‐Brook rearrangement/vinylogous Michael reaction cascade. These adducts can then undergo a diastereoselective deprotection/intramolecular Henry sequence to rapidly assemble densely functionalized nitrocyclopentanols with three contiguous stereocenters (see scheme; TES=triethylsilyl).