Reductive sulfenylation. A general method for the .alpha.-sulfenylation of cyclic ketones

Synthesis and evaluation of a broad range of chiral sulfides for asymmetric sulfur ylide epoxidation of aldehydes

“…The aqueous layer was extracted with ether (3 × 50 cm 3 ). The combined organic extracts were washed with saturated sodium bicarbonate solution (50 cm 3 ) and brine (50 cm 3 ), dried (MgSO 4 ), concentrated under reduced pressure and purified by flash column chromatography (ether-petrol 10 : 90) to afford 28a (530 mg, 60%) as a yellow oil; [α] 22 D = ϩ3.6 (c 0.55 in CHCl 3 ); ν max (film)/cm Ϫ1 2975, 2928, 2869, 1453, 1381 and 1364; δ H (250 MHz; CDCl 3 ) 1.13 (3H, d, J 7.0, CH 3 CH), 1.39 (3H, s, CH 3 C), 1.48 (3H, s, CH 3 C), 2.40 (1H, d, J 13.0, CHHS), 2.80-3.00 (2H, m, CHS and CHHS), 3.57 (1H, dd, J 12.0 and 10.0, CHHO) and 3.92 (1H, dd, J 12.0 and 3.0, CHHO); δ C (63 MHz; CDCl 3 ) 16.4, 22.1, 29.2, 34.1, 37.4, 68.5 and 69.1; m/z (CI) 147 (M ϩ , 100%), 88 (34), 71 (15), 63 (31) and 58 (28)…”

Towards the Iodine‐Catalyzed Regioselective Sulfenylation of Unsymmetrical Ketones

“…In recent years, a number of methods have been developed for the direct formation of stereogenic carbon centers bearing a sulfur atom. The α‐sulfenylation of carbonyl compounds, such as ketones, lactams, esters, and amides, has also been achieved. All of these methods involve the formation of a metalloenolate or enamine precursor, which is followed by reaction with a sulfur‐based reagent to produce the α‐thio‐functionalized carbonyl compound .…”