2005
DOI: 10.1002/ejoc.200400766
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Reaction of Thioketones with (R)‐2‐Vinyloxirane: Regio‐ and Stereoselective Formation of (S)‐4‐Vinyl‐1,3‐oxathiolanes

Abstract: The reactions of 4,4'‐dimethoxythiobenzophenone (1), 9H‐xanthene‐9‐thione (2), and adamantane‐2‐thione (3) with (R)‐2‐vinyloxirane [(R)‐6] in the presence of SiO2 in anhydrous CH2Cl2 at 0 °C or room temperature afforded the corresponding 4‐vinyl‐1,3‐oxathiolane derivatives (S)‐7, (S)‐9, and (S)‐11, respectively. The analogous BF3‐catalyzed reactions of (R)‐6 with 1,1,3,3‐tetramethylindane‐2‐thione (4) and 2,2,4,4‐tetramethyl‐3‐thioxocyclobutanone (5) in anhydrous CH2Cl2 at –65 °C or –78 °C yielded the correspo… Show more

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Cited by 9 publications
(7 citation statements)
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“…General. See [7] [17]. Optical rotations were recorded on a Perkin-Elmer-241 polarimeter (c = 1, in THF).…”
Section: Scheme 8 Schemementioning
confidence: 99%
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“…General. See [7] [17]. Optical rotations were recorded on a Perkin-Elmer-241 polarimeter (c = 1, in THF).…”
Section: Scheme 8 Schemementioning
confidence: 99%
“…13 C-NMR (125.8 MHz, CDCl 3 ): 138.8 (d, CH=CH 2 ); 114.5 (t, CH=CH 2 ); 105.1 (s, C(2)); 73.6 (t, C(5')); 53.9 (s, C(1)); 52.6 (d, C(4')); 50.1 (t, C(3)); 48.5 (s, C(7)); 46.2 (d, C(4)); 30.2 (t, C(6)); 27.4 (t, C(5)); 21.0 (q, Me syn ), 20.2 (q, Me anti ); 14.1 (q, MeÀC (1)). ESI-MS (MeOH + NaI): 277 (28, [M + K] + ), 263 (14), 262 (18), 261 (100, [M + Na] + ), 245 (24), 229 (7), 207 (11). Anal.…”
Section: Scheme 8 Schemementioning
confidence: 99%
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“…336 de Thioketones such as 4,4 -dimethoxythiobenzophenone react with enantiopure (R)-2-vinyloxirane to give virtually enantiopure (S)-4-vinyl-1,3-oxathiolanes (86) in high ee yield, using mild Lewis acid conditions (SiO 2 , DCM, 0 • C). 337 More hindered thioketones require a stronger Lewis acid (BF 3 , −78 • C). The clear inversion at the oxirane C(2) indicates an efficient S N 2 mechanism.…”
Section: Other Reactionsmentioning
confidence: 99%