Dichloromethane → (R)-methyl 4-(2-(3-((tert-butyldimethylsilyl)oxy)-5-oxocyclopent-1-en-1-yl)ethyl)benzoate

Participants

Reaction Steps

A solution of 9-BBN (6.95 g, 28.5 mmol) in 110 mL THF was cannula transferred to a solution of methyl 4-vinylbenzoate (4.65 g, 28.7 mmol) in 22 mL THF, rinsing with 10 mL THF. The reaction was stirred at room temperature for 4 h, was cooled to 0° C. and 5.4 mL H2O was added. After 45 minutes at room temperature, the solution was cannula transferred to a mixture of the (R)-4-((tert-butyldimethylsilyl)oxy)-2-iodocyclopent-2-enone (8 g, 24 mmol) and PdCl2(dppf).CH2Cl2 (1.76 g, 2.41 mmol) in DMF (70 mL). The reaction was stirred for 5 minutes and then a solution of K3PO4 (9.6 mL, 28.8 mmol, 3 M) was added. The resulting dark mixture was allowed to stir overnight and then was partitioned between ethyl acetate/H2O. The organic solution was washed further with H2O (2×) and brine and then was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (ethyl acetate/hexanes) gave the title compound (6.81 g).

Provenance & Evidence