Synlett 2004(6): 995-998  
DOI: 10.1055/s-2004-820054
LETTER
© Georg Thieme Verlag Stuttgart · New York

Arenesulfinamides as New Reagents for the Synthesis of Allylic Sulfoxides

Mateo Alajarín*, Aurelia Pastor*, José Cabrera
Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, Campus de Espinardo, 30100 Murcia, Spain
Fax: +34(968)364149; e-Mail: alajarin@um.es;
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Publikationsverlauf

Received 12 February 2004
Publikationsdatum:
25. März 2004 (online)

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.

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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 CH2Cl2 (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 Et2O/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. 1H NMR (200 MHz, CDCl3): δ = 2.38 (s, 3 H, CH 3 ), 3.82 (d, 1 H, 2 J = 12.7 Hz, CH 2 SO), 4.07 (d, 1 H, 2 J = 12.7 Hz, CH 2 SO), 5.09 (s, 1 H, = CH 2 ), 5.53 (s, 1 H, = CH 2 ), 7.23-7.49 (m, 9 H, aromatics). 13C {1H} NMR (50 MHz, CDCl3): δ = 21.3 (q), 64.7 (t), 119.7 (t), 124.3 (2 × d), 126.0 (2 × d), 128.0 (d), 128.4 (2 × d), 129.5 (2 × d), 137.5 (s), 138.9 (s), 140.2 (s), 141.6 (s). Anal. Calcd for C16H16SO: C, 74.96; H, 6.29; S, 12.51. Found: C, 74.72; H, 6.47; S, 12.20.