J. Chen et al. / Tetrahedron Letters 49 (2008) 6921–6923
6923
7066; (e) Grainger, R. S.; Welsh, E. J. Angew. Chem., Int. Ed. 2007, 46, 5020; (f)
Sun, X. W.; Liu, M.; Xu, M. H.; Lin, G. Q. Org. Lett. 2008, 10, 1259.
References and notes
18. (a) Owens, T. D.; Souers, A. J.; Ellman, J. A. J. Org. Chem. 2003, 68, 3; (b) Schenkel,
L. B.; Ellman, J. A. Org. Lett. 2003, 5, 545; (c) Souers, A. J.; Owens, D. T.; Ellman,
A. J. Inorg. Chem. 2001, 40, 5299; (d) Schenkel, L. B.; Ellman, J. A. J. Org. Chem.
2004, 69, 1800; (e) Mancheno, O. G.; Priego, J.; Cabrera, S.; Arrayas, R. G. J. Org.
Chem. 2003, 68, 3679; (f) Fur, N. L.; Mojovic, L.; Ple, N.; Turck, A.; Reboul, V.;
Metzner, P. J. Org. Chem. 2006, 71, 2609.
1. For reviews see: (a) Bloch, R. Chem. Rev. 1998, 98, 1407; (b) Kobayashi, S.;
Ishitani, H. Chem. Rev. 1999, 99, 1069; (c) Ellman, J. A.; Owens, T. D.; Tang, T. P.
Acc. Chem. Res. 2002, 35, 984; (d) Enders, D.; Reindhold, U. Tetrahedron:
Asymmetry 1997, 8, 1895; (e) Brase, S.; Baumann, T.; Dahmen, S.; Vogt, H. Chem.
Commun. 2007, 1881; (f) Friestad, G. K.; Mathies, A. K. Tetrahedron 2007, 63,
2541; (g) Ferraris, D. Tetrahedron 2007, 63, 9581.
2. Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001,
123, 984.
3. Fujihara, H.; Nagai, K.; Tomioka, K. J. Am. Chem. Soc. 2000, 122, 12055.
4. Shi, M.; Wang, C. J. Adv. Synth. Catal. 2003, 345, 971.
5. Boezio, A. A.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 1692.
6. (a) Cote, A.; Boezio, A. A.; Charette, A. B. Angew. Chem., Int. Ed. 2004, 43, 6525;
(b) Boezio, A. A.; Pytkowicz, J.; Cote, A.; Charette, A. B. J. Am. Chem. Soc. 2003,
125, 14260; (c) Cote, A.; Boezio, A. A.; Charette, A. B. Proc. Natl. Acad. Sci. 2004,
101, 5405; (d) Lauzon, C.; Charette, A. B. Org. Lett. 2006, 8, 2743.
7. Dahmen, S.; Brase, S. J. Am. Chem. Soc. 2002, 124, 5940.
8. Nishimura, T.; Yasuhara, Y.; Hayashi, T. Org. Lett. 2006, 8, 979.
9. Weix, D. J.; Shi, Y.; Ellman, J. A. J. Am. Chem. Soc. 2005, 127, 1092.
10. Grushin, V. V. Chem. Rev. 2004, 104, 1629.
11. Selective examples: (a) Trost, B. M.; Breit, B.; Organ, M. G. Tetrahedron Lett.
1994, 35, 5817; (b) Clayden, J.; Johnson, J. P.; Pink, J. H.; Helliwell, M. J. Org.
Chem. 2000, 65, 7033; (c) Gilbertson, S. R.; Lan, P. Org. Lett. 2001, 3, 2237; (d)
Dai, W. M.; Yeung, K.; Liu, J. T.; Zhang, Y.; Williams, I. D. Org. Lett. 2002, 4, 1615.
12. Cote, A.; Charette, A. B. J. Org. Chem. 2005, 70, 10864.
13. Mellah, M.; Voituriez, A.; Schulz, E. Chem. Rev. 2007, 107, 5133.
14. (a) Hiroi, K.; Suzuki, Y.; Kawagishi, R. Tetrahedron Lett. 1999, 40, 715; (b) Hiroi,
K.; Suzuki, Y.; Abe, I.; Kawagishi, R. Tetrahedron 2000, 56, 4701; (c) Hiroi, K.;
Suzuki, Y.; Kaneko, Y.; Kato, F.; Abe, I.; Kawagishi, R. Polyhedron 2000, 19, 525.
15. (a) Kagan, H. B. Rev. Heteroat. Chem. 1992, 7, 92; (b) Calligaris, M. Coord. Chem.
Rev. 2004, 248, 351; (c) Alessio, E. Chem. Rev. 2004, 104, 4203.
19. Liao, J.; Sun, X. X.; Cui, X.; Yu, K. B.; Zhu, J.; Deng, J. G. Chem. Eur. J. 2003, 9, 2611.
20. Characterization data of 4a–c: Compound 4a: Colorless oil. ½a D25
ꢀ13.2 (c 0.4,
ꢂ
EtOH). 1H NMR (CDCl3): d 7.92–7.95 (br, 1H), 7.45 (t, J = 7.3 Hz, 1H), 6.99–7.31
(m, 12H), 1.26 (s, 9H). 13C NMR (CDCl3): d 161.7, 151.1, 150.7, 137.1, 134.4,
134.3, 132.7, 132.5, 132.4, 132.1, 131.8, 131.3, 128.1, 127.9, 127.8, 127.7 119.4,
119.2, 114.1, 58.3, 55.1, 24.0. 31P NMR (CDCl3): d ꢀ14.6; IR (liquid film) (cmꢀ1
)
3051, 2960, 2921, 1582, 1432, 1432, 1047, 741,694. HRMS: calcd for
C22H23OPS+Na: 389.1099, found: 389.1111.
Compound 4b: White solid. ½a D25
ꢂ
ꢀ165.1 (c 0.1, EtOH), mp: 114–115 °C. 1H NMR
(CDCl3): 7.21–7.61 (m, 12H), 6.93 (d, J = 8.0 Hz 1H), 3.32 (s, 3H),1.22 (s, 9H). 13
C
NMR (CDCl3): d 161.6, 161.5, 150.9, 150.5, 137.2, 134.3, 132.6, 132.4, 132.3,
132.2, 132.1, 130.4, 130.3, 130.2, 128.0, 127.9, 127.8, 127.7, 127.6, 119.2, 119.1,
114.0, 55.0, 23.9. 31P NMR (CDCl3): d ꢀ18.7; IR (KBr) (cmꢀ1): 3058, 2978, 1570,
1453, 1451, 1264, 1176, 1039, 1025, 789, 743, 693. HRMS: calcd for
C23H25O2PS+Na: 419.1205, found: 419.1210.
Compound 4c: White solid. ½a D25
ꢂ
ꢀ195.2 (c 0.1, EtOH), mp: 117–118 °C. 1H NMR
(CDCl3): d 7.21–7.72 (m, 13H), 4.61 (m, 2H), 2.95 (s, 3H), 1.23(s, 9H). 13C NMR
(CDCl3): d 59.6, 151.0, 150.6, 137.1, 136.9, 134.0, 133.9, 132.4, 132.3, 132.2,
132.1, 130.6, 130.4, 130.2, 128.0, 127.9, 127.8, 127.7, 120.4, 120.1, 116.5, 94.0,
58.3, 55.7, 23.8. 31P NMR (CDCl3): d ꢀ18.5. IR (KBr) (cmꢀ1): 3056, 2970, 2896,
1571, 1435, 1252, 1152, 1137, 1079, 1031, 998, 789, 750, 693. HRMS: calcd for
C24H28O3PS+H: 427.1491, found: 427.1496.
21. Copper(II) trifluoroacetate hydrate(Cu(O2CCF3)2ꢁxH2O) was purchased from
Alfa Aesar, x = 0.56. For literatures about improving enantioselectivities of
dialkylzinc addition by adding trace water or by using metal complex hydrate,
see: (a) Keller, E.; Maurer, J.; Naasz, R.; Schader, T.; Meetsma, A.; Feringa, B. L.
Tetrahedron: Asymmetry 1998, 9, 2409; (b) Delapierre, G.; Constantieux, T.;
Brunel, J. M.; Buono, G. Eur. J. Org. Chem. 2000, 2507; (c) Alexakis, A.; Benhaim,
C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262.
16. Owens, T. D.; Hollander, F.; Oliver, A.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123,
1539.
17. Selected literatures for applications of tert-butanesulfinamide: (a) Kochi, T.;
Tang, T. P.; Ellman, J. A. J. Am. Chem. Soc. 2003, 125, 11276; (b) Kells, K. W.;
Chong, J. M. J. Am. Chem. Soc. 2004, 126, 15666; (c) Zhong, Y. W.; Dong, Y. Z.;
Fang, K.; Izumi, K.; Xu, M. H.; Lin, G. Q. J. Am. Chem. Soc. 2005, 127, 11956; (d)
Unthank, M. G.; Hussain, N.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2006, 45,
22. Andersson, P. G.; Guijarro, D.; Tanner, D. J. Org. Chem. 1997, 62, 7364.