2-[3-(tert-Butyldimethylsiloxy)-1,2-syn-dideuteriopropyl]-2-cyclohexen-1-one(syn-7). Propene cis–2 (150mg, 0.86 mmol) was added to a solution of 9-BBN (126 mg, 1.03 mmol) in THF (15mL) at 0 °C. The reactionmixture was heated to reflux for 12 h.  Themixture was cooled to 25 °C, and2-iodo-2-cyclohexene-1-one (229 mg, 1.03 mmol), Pd(dppf)Cl2 (14 mg, 0.017mmol), and NaOH (0.6 mL, 3 M,aqueous) were added sequentially.  Themixture was again brought to reflux where it remained for 2 h. The reaction mixturewas partitioned between NaCl (75 mL, saturated aqueous) and Et2O (50 mL). Theaqueous phase was separated and washed with 2 _ 25 mL of Et2O. The combinedorganic layers were dried over Na2SO4, filtered, and reduced in vacuo.  Purification by flash chromatography (10:90EtOAc:hexane) yielded pure product as a colorless oil (119 mg, 51%).

【Ridgway, B. H.;Woerpel, K. A. J. Org. Chem. 1998, 63,458–460】