Y. Watanabe et al. / Tetrahedron: Asymmetry 10 (1999) 737–745
745
4.17. tert-Butyl p-toluenesulfinate 2o17
Purification of the crude product was performed by column chromatography (hexane:ethyl ace-
1
tate=90:10) to afford sulfinate 2o in 83% yield. H NMR (CDCl3) δ 1.55 (s, 9H), 2.41 (s, 3H), 7.31
(d, J=8.0 Hz, 2H), 7.56 (d, J=8.0 Hz, 2H); IR (KBr) 2975, 2925, 1600, 1500, 1450, 1395, 1370, 1250,
1170, 1130, 1110, 1080, 860, 790, 720 cm−1.
References
1. (a) Mikolajczk, M.; Drabowicz, J.; Kielbasinski, P. Chiral Sulfur Reagents; CRC Press: Boca Raton, 1997. (b) Capozzi, G.;
Drabowicz, J.; Kielbasinnski, P.; Menichetti, S.; Mikolajczyk, M.; Nativi, C.; Schank, K.; Schott, N.; Zoller, U. Syntheses
of Sulphones, Sulphoxides and Cyclic Sulphides; Patai, S. and Rappoport, Z. Ed.; John Wiley: New York, 1994. (c) Solladie,
G. In Comprehensive Organic Synthesis, Trost, B. M. Ed.; Pergamon: Oxford, 1991; Vol. 6; Chap. 1.5. (d) Walker, A. J.
Tetrahedron: Asymmetry 1992, 3, 961. (e) Posner, G. H. Acc. Chem. Res. 1987, 20, 72. (f) Solladie, G. Synthesis 1981,
185.
2. (a) Andersen, K. K.; Gaffield, W.; Papanikolau, N. E.; Foley, J. W.; Perkins, R. I. J. Am. Chem. Soc. 1964, 86, 5637 and
references cited therein.
3. (a) Kagan, H. B. Synlett 1990, 643. (b) Pitchen, P.; Kagan, H. B. Tetrahedron Lett. 1984, 25, 1049. (c) Pitchen, P.; Dunach,
E.; Deshmukh, M. N.; Kagan, H. B. J. Am. Chem. Soc. 1984, 106, 8188. (d) Ohta, H.; Okamoto, Y.; Tsuchihashi, G. Chem.
Lett. 1984, 205. (e) Komatsu, N.; Nishibayashi, Y.; Sugita, T.; Uemura, S. Tetrahedron Lett. 1992, 33, 5391. (f) Komatsu,
N.; Hashizawa, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 4529.
4. (a) Miyaji, Y.; Minato, H.; Kobayashi, M. Bull. Chem. Soc. Jp. 1971, 44, 862. (b) Furukawa, M.; Okawara, T.; Noguchi,
Y.; Nishikawa, M. Synthesis 1978, 441. (c) Boar, R. B.; Patel, A. C. Synthesis 1982, 584.
5. (a) Philips, H. J. Chem. Soc. 1925, 127, 2552. (b) Estep, R. E.; Tavares, D. R. Int. J. Sulfur Chem. 1973, 8, 279. (c) Wilt,
J. W.; Stein, R. G.; Wagner, W. J. J. Org. Chem. 1967, 32, 2097. (d) Harpp, D. N.; Friedlander, B. T.; Larsen, C.; Steliou,
K.; Stockton, A. J. Org. Chem. 1978, 43, 3481. (e) Whitesell, J. K.; Wong, M.-S. J. Org. Chem. 1991, 56, 4552.
6. (a) Fernandez, I.; Khiar, N.; Llera, J. M.; Alcudia, F. J. Org. Chem. 1992, 57, 6789. (b) Field, L.; Hoelzel, C. B.; Locke, J.
M. J. Am. Chem. Soc. 1962, 84, 847.
7. (a) Solladié, G.; Hutt, J.; Girardin, A. Synthesis 1987, 173 and references sited therein. (b) Kobayashi, M.; Terao, M. Bull.
Chem. Soc. Jp. 1966, 39, 1292. (c) Meek, J. S.; Fowler, J. S. J. Org. Chem. 1968, 33, 3422.
8. Klunder, J. M.; Sharpless, K. B. J. Org. Chem. 1987, 52, 2598.
9. Whitesell, J. K.; Wong, M.-S. J. Org. Chem. 1994, 59, 597
10. (a) Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794. (b) Toru, T.; Watanabe, Y.; Mase, N.; Tsusaka,
M.; Hayakawa, T.; Ueno, Y. Pure and Appl. Chem. 1996, 68, 711. (c) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am.
Chem. Soc. 1993, 115, 10464.
11. Diacetone-D-glucosyl 2,4,6-triisopropylbenzenesulfinate 2a was not obtainable from bis(2,4,6-triisopropylbenzene)
disulfide according to the Alcudia’s method (Ref. 6a), because the reaction of bis(2,4,6-triisopropylbenzene) disulfide
with sulfuryl chloride gave thiol sulfinate in quantitative yield instead of sulfinyl chloride.
12. Whitmore, F. C.; Hamilton, F. H. Org. Synth. 1941, 492.
13. (a) Khiar, N.; Fernandez, I.; Alcudia, F. Tetrahedron Lett. 1994, 35, 5719. (b) Llera, J. M.; Fernandez, I.; Alcudia, F.
Tetrahedron Lett. 1991, 32, 7299.
14. Diastereomerically pure 2,4,6-trimethylbenzenesulfinate can be obtained by the reported method, see: Rebiere, F.; Samuel,
O.; Ricard, L.; Kagan, H. B. J. Org. Chem. 1991, 56, 5991.
15. Herbrandson, H. F.; Dickerson Jr., R. T. J. Am. Chem. Soc. 1959, 81, 4102.
16. Posner, G. H.; Mallamo, J. P.; Hulce, M.; Frye, L. L. J. Am. Chem. Soc. 1982, 104, 4180.
17. Boar, R. B.; Patel, A. C. Synthesis 1982, 584.