Abstract
Reaction of arenesulfinamides with alkenes bearing allylic hydrogens in the presence of Yb(OTf)3 /TMSCl led to the corresponding allylic sulfoxides in good yields.
Key word
alkenes - sulfinamides - lanthanides - regioselectivity - sulfoxides
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Typical Procedure for the Synthesis of Allylic Sulfoxides 3: To a solution of p -toluenesulfinamide 1a (0.15 g; 0.966 mmol) in dry CH2 Cl2 (20 mL), Yb(OTf)3 (0.30 g; 0.483 mmol), α-methyl styrene (0.34 g; 2.899 mmol) and TMSCl (0.11 g; 0.966 mmol) were sequentially added. After the addition, the reaction mixture was stirred at r.t. for 16 h. The inorganic salts were removed by filtration and the filtrate was collected. The solvent was evaporated to dryness and the residue purified by silica gel chromatography eluting with 1:3 to 1:1 EtOAc-hexanes. An analytically pure sample was obtained by recrystallization from Et2 O/n -pentane (white prisms). Yield (0.22 g, 90%); mp 63-65 °C. IR (neat): 1620, 1597, 1494, 1085, 1045, 810, 778, 701 cm-1 . 1 H NMR (200 MHz, CDCl3 ): δ = 2.38 (s, 3 H, CH
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