Stereoselective Synthesis of Sex Pheromone (R)‐4‐Methyl‐1‐Nonanol: Non‐Cross‐Linked Polystyrene Supported Oxazolidinone as a Chiral Auxiliary

Abstract ( R )‐4‐Methyl‐1‐nonanol, the sex pheromone of the yellow mealworm ( Tenebrio Molitor L.), was synthesized by using non‐cross‐linked polystyrene supported oxazolidinone as a chiral auxiliary. The stereoselective synthesis was achieved by asymmetric Michael addition of an organocopper reagent to non‐cross‐linked polystyrene supported N ‐crotonoyoxazolidinone, and the target product was obtained in an overall yield of 41.8 % over seven steps with a high enantiomeric excess of 98 %.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)