1040
C.-J. Wang et al. / Tetrahedron Letters 50 (2009) 1038–1040
T.; Hashimoto, K.; Hatsuda, M.; Oku, A. J. Org. Chem. 2000, 65, 1335; (d) Itoh, T.;
Chika, J.-I. J. Org. Chem. 1995, 60, 4968.
tuted b-keto esters. Further applications of the new ligand in other
transition metal-catalyzed reactions are underway, and will be dis-
closed in due course.
12. For a 4,40-disubstituted BINAP, see: Ngo, H. L.; Lin, W. J. Org. Chem. 2005, 70,
1177; For a 5,50-derivative, see: Deng, G.; Fan, Q.; Chen, X.; Liu, D.; Chan, A. S.
Chem. Commun. 2002, 1570; For a 6,60-derivative, see: Ngo, H. L.; Hu, A.; Lin, W.
Chem. Commun. 2003, 1912; For a 7,70-derivative, see: Che, D.; Andersen, N. G.;
Lau, S. Y. W.; Parvez, M.; Keay, B. A. Tetrahedron: Asymmetry 2000, 11, 1919.
13. For recent reviews, see: (a) Xie, J.; Zhou, Q. Acc. Chem. Res. 2008, 41, 581; (b)
Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029; (c) Zhang, W.; Chi, Y.; Zhang, X.
Acc. Chem. Res. 2007, 40, 1278.
Acknowledgments
This work was supported by National NaturalScience Foundation
of China (20702039) and the startup fund from Wuhan University.
14. Characterization data of 3–8:Compound 3: Colorless oil. IR (KBr)
m
2963, 2869,
1599, 1567, 1453, 1421, 1277, 1054, 831, 693, 584 cmꢀ1
;
1H NMR (CDCl3, TMS,
300 MHz) d 1.28 (s, 9H), 3.78 (s, 3H), 6.85 (s, 2H), 7.10 (s, 1H); 13C NMR (CDCl3,
TMS, 75 MHz) d 31.11, 34.93, 55.40, 111.26, 113.40, 121.28, 122.53, 154.58,
160.08; MS (EI) m/z 242 ([M]+).Compound 4: An off-white solid. Mp 106–
References and notes
1. (a)Catalytic Asymmetric Synthesis; Ojima, I., Ed., 2nd ed.; Wiley-VCH: Weinheim,
2000; (b)Comprehensive Asymmetric Catalysis I–III; Jacobsen, E. N., Pfaltz, A.,
Yamamoto, H., Eds.; Springer: Berlin, 1999; (c) Noyori, R. Asymmetric Catalysis
in Organic Synthesis; Wiley: New York, 1994.
2. (a) Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori,
R. J. Am. Chem. Soc. 1980, 102, 7932; (b) Noyori, R. Angew. Chem., Int. Ed. 2002,
41, 2008.
3. Schmid, R.; Broger, E. A.; Cereghtti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.;
Muller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. Pure Appl. Chem. 1996, 68, 131.
4. (a) Zhang, Z.; Qian, H.; Longmire, J.; Zhang, X. J. Org. Chem. 2000, 65, 6223; (b)
Wu, S.; Wang, W.; Tang, W.; Lin, M.; Zhang, X. Org. Lett. 2002, 4, 4495; (c) Tang,
W.; Wu, S.; Zhang, X. J. Am. Chem. Soc. 2003, 125, 9570; (d) Lei, A.; Wu, S.; He,
M.; Zhang, X. J. Am. Chem. Soc. 2004, 126, 1626; (e) Wang, C.-J.; Sun, X.; Zhang,
X. Angew. Chem. 2005, 117, 5013. Angew. Chem., Int. Ed. 2005, 44, 4933; (f)
Wang, C.-J.; Sun, X.; Zhang, X. Synlett 2006, 1169; (g) Raghunath, M.; Zhang, X.
Tetrahedron Lett. 2005, 46, 7017.
5. (a) Qiu, L.; Li, Y.; Kwong, F.; Yu, W.; Fan, Q.; Chan, A. S. C. Adv. Synth. Catal. 2007,
349, 517; (b) Pai, C.-C.; Lin, C.-W.; Lin, C.-C.; Chen, C.-C.; Chan, A. S. C.; Wong,
W. T. J. Am. Chem. Soc. 2000, 122, 11513.
6. Saito, T. ; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.; Miura, T.; Kumobayashi,
H. Adv. Synth. Catal. 2001, 343, 264.
7. (a) Pai, C. C.; Li, Y. M.; Zhou, Z. Y.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 2789;
(b) Paule, S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genêt, J. P.; Champion, N.;
Dellis, P. Eur. J. Org. Chem. 2003, 1931.
8. Jeulin, S.; Paule, S.; Ratovelomanana-Vidal, V.; Genêt, J. P.; Champion, N.; Dellis,
P. Angew. Chem., Int. Ed. 2004, 43, 320.
108 °C; IR (KBr)
m: 2959, 2868, 1597, 1577, 1453, 1438, 1186, 1060, 860, 757,
695 cmꢀ1 1H NMR (CDCl3, TMS, 300 MHz) d 1.24 (s, 9H), 3.77 (s, 3H), 6.99 (d,
;
J = 13.8 Hz, 1H), 7.10 (s, 1H), 7.26 (d, J = 13.2 Hz, 1H), 7.40–7.60 (m, 6H), 7.63–
7.69 (m, 4H); 13C NMR (CDCl3, TMS, 75 MHz) d 31.35, 35.17, 55.56, 113.41,
113.56, 122.01, 122.15, 128.60, 128.76, 131.51, 131.18, 131.31, 133.44, 133.82,
153.52, 153.69, 159.46, 159.67; 31P NMR (CDCl3, 85% H3PO4, 242.86 MHz) d
31.05; HRMS calcd for C23H25O2P: 364.1591, found: 364.1592.Compound 5: An
off-white solid. Mp 112–115 °C; IR (KBr)
m
2962, 2905, 868, 1577, 1458, 1438,
1186, 1055, 850, 758, 698, 504 cmꢀ1
;
1H NMR (CDCl3, TMS, 300 MHz) d 1.14 (s,
9H), 3.91 (s, 3H), 6.83 (dd, J = 14.0 and 2.3 Hz,, 1H), 6.98 (d, J = 1.2 Hz, 1H), 7.48
(m, 4H), 7.56 (m, 2H), 7.74 (m, 4H); 13C NMR (CDCl3, TMS, 75 MHz) d 31.09,
35.11, 57.01, 88.91–159.02 (m); 31P NMR (CDCl3, 85% H3PO4, 242.86 MHz) d
35.46; HRMS calcd for C23H24IO2P+H+: 491.0637, found: 491.0631.Compound
6: An off-white solid. Mp 207–210 °C; IR (KBr)
m 3439, 2963, 2760, 1577, 1458,
1438, 1166, 1010, 784, 751, 695, 515 cmꢀ1 1H NMR (CDCl3, TMS, 300 MHz) d
;
1.07 (s, 9H), 6.43 (s, 1H), 6.66 (dd, J = 14.6 and 1.2 Hz, 1H), 7.21 (d, J = 1.2 Hz,
1H), 7.48 (m, 4H), 7.52 (m, 2H), 7.71 (m, 4H); 13C NMR (CDCl3, TMS, 75 MHz) d
29.75, 33.52, 85.68–155.98 (m); 31P NMR (CDCl3, 85% H3PO4, 242.86 MHz) d
36.25; HRMS calcd for C22H22IO2P+H+: 477.0480, found: 477.0471.Compound
7: An off-white solid. Mp 239–240 oC; ½a D25
ꢁ
ꢀ86.2 (c 0.19, CHCl3); IR (KBr)
m
2961, 2902, 2869, 1589, 1554, 1478, 1196, 1012, 782, 752, 697, 507 cmꢀ1
;
1H
NMR (CDCl3, TMS, 300 MHz) d 0.98 (s, 18H), 1.33 (d, J = 5.7 Hz, 6H), 2.12 (m,
2H), 4.85 (m, 2H), 6.73(d, J = 14.7 Hz, 2H), 6.87 (s, 2H), 7.76 (m,10H); 13C NMR
(CDCl3, TMS, 75 MHz) d 20.38, 31.05, 34.93, 45.13, 73.15, 90.86–157.58 (m);
31P NMR (CDCl3, 85% H3PO4, 242.86 MHz)
d 35.29; HRMS calcd for
C49H52I2O4P2+H+: 1021.1516, found: 1021.1503Compound 8: An off-white
solid. Mp 85–87 oC; ½a D25
ꢁ
+124.7 (c 0.40, CHCl3); IR (KBr)
m
2964, 2905, 2869,
;
9. For reviews: (a) Xie, J.; Zhu, S.; Fu, Y.; Hu, A.; Zhou, Q. Pure Appl. Chem.
2005, 77, 2121; (b) McCarthy, M.; Guiry, P. J. Tetrahedron 2001, 57, 3809;
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T. T.-L.; Chan, S.-S.; Chan, A. S. C. Adv. Synth. Catal. 2003, 345, 537; (e)
Shimizu, H.; Nagasaki, I.; Saito, T. Tetrahedron 2005, 61, 5405; (f) Wei, H.;
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(g) Wei, H.; Zhang, Y.; Wang, F.; Zhang, W. Tetrahedron: Asymmetry 2008,
19, 482; (h) Sun, Y.; Wan, X.; Guo, M.; Wang, D.; Dong, X.; Pan, Y.; Zhang,
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D.; Zhang, Z. J. Org. Chem. 2005, 70, 1070.
1591, 1558, 1479, 1438, 1187, 1026, 995, 878, 751, 695 cmꢀ1
1H NMR (CDCl3,
TMS, 300 MHz) d 1.13 (s, 18H), 1.25 (d, J = 3.6 Hz, 6H), 1.65 (m, 2H), 2.26 (m,
2H), 4.34 (m, 2H), 6.74 (s, 2H), 6.94 (d, J = 13.2 Hz, 2H), 7.32 (m,10H); 13C NMR
(CDCl3, TMS, 75 MHz) d 22.33, 31.13, 34.87, 40.918, 75.715, 118.5–157.31 (m);
31P NMR (CDCl3, 85% H3PO4, 242.86 MHz)
C49H52O4P2+H+: 767.3419, found: 767.3440.
d 24.52; HRMS calcd for
15. Takaya, H.; Akutagawa, S.; Noyori, R. Org. Synth. 1993, 71, 57.
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