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H. Shimizu et al. / Tetrahedron: Asymmetry 15 (2004) 2169–2172
2H), 1.28 (dd, J ¼ 12.6, 23.1 Hz, 2H), 0.89 (d, J ¼ 6.6 Hz,
References and notes
6H), 0.88 (d, J ¼ 6.6 Hz, 6H), 0.71 (d, J ¼ 6.6 Hz, 6H),
0.68 (d, J ¼ 6.6 Hz, 6H); 31P NMR (CD2Cl2) d )27.0; EI-
1. For a recent review: Tang, W.; Zhang, X. Chem. Rev.
2003, 103, 3029.
MS m=z 554(M) þ; ½aꢀ ¼ )226.5 (c 1.0, CHCl3 98.8% ee).
D
10. Diphospholane ligands with biaryl backbone were synthe-
sized by Schmid and Achiwa (a) Schmid, R.; Broger, E.
A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.;
2. Blaser, H.-U.; Malan, C.; Pugin, B.; Spindler, F.; Steiner,
H.; Studer, M. Adv. Synth. Catal. 2003, 345, 103.
3. Koening, K. E.; Sabacky, M. J.; Bachman, G. L.;
Christopfel, W. C.; Barnstorff, H. D.; Friedman, R. B.;
Knowles, W. S.; Stultz, B. R.; Vineyard, B. D.; Weinkauff,
D. J. Ann. N.Y. Acad. Sci. 1980, 16, 333.
€
Muller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. Pure
Appl. Chem. 1996, 68, 131; (b) Fujie, N.; Matsui, M.;
Achiwa, K. Chem. Pharm. Bull. 1999, 47, 436.
11. (aS,S,S)-(4,40-Bi-1,3-benzodioxole)-5,50-diylbis(2,5-di-meth-
ylphospholane) (aS,S,S)-2: Mp 163–165 °C; 1H NMR
(CDCl3): d 7.19 (dd, J ¼ 3.3, 8.2 Hz, 2H), 6.95 (d,
J ¼ 8.2 Hz, 2H), 6.03 (m, 2H), 5.98 (d, J ¼ 1.1 Hz, 2H),
2.65–2.50 (m, 2H), 2.42–2.26 (m, 2H), 2.23–2.05 (m, 4H),
1.64(dddd, J ¼ 2.2, 4.9, 13.2, 24.2 Hz, 2H), 1.50–1.37 (m,
2H), 1.33 (dd, J ¼ 7.1, 18.1 Hz, 6H), 0.90 (dd, J ¼ 7.1,
10.4, 6H); 31P NMR (CDCl3): d )2.3; EI-MS m=z 469
4. Lipkowitz, K. B.; Kozlowski, M. C. Synlett 2003,
1547.
5. MM2 calculation was carried by CAChe.
6. (a) Burk, M. J. Am. Chem. Soc. 1991, 113, 8518; (b) Burk,
M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am.
Chem. Soc. 1993, 115, 10125.
7. Saito, T.; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.;
Miura, T.; Kumobayashi, H. Adv. Synth. Catal. 2001, 343,
264.
(M)H)þ; ½aꢀ ¼ +255.4( c 1.0, CHCl3).
D
12. (+)-(4,40-Bi-1,3-benzodioxole)-5,50-diylbis(diisopropyl-phos-
ꢀ
8. Our calculation afforded values below; 1: d ¼ 8.36 A,
1
ꢀ
ꢀ
ꢀ
phine) (+)-3: Mp 84–86 °C; H NMR (CDCl3): d 7.03 (d,
r ¼ 4.18 A, h ¼ 33.4°; 2: d ¼ 7.44 A, r ¼ 3.73 A,
ꢀ
ꢀ
J ¼ 7.9 Hz, 2H), 6.88 (d, J ¼ 7.9 Hz, 2H), 5.95 (2H,
J ¼ 1.5 Hz, 2H), 5.80 (d, J ¼ 1.5 Hz, 2H), 2.19–2.06 (m,
2H), 1.84–1.72 (m, 2H), 1.10 (dd, J ¼ 7.1, 14.2 Hz, 6H),
1.07 (dd, J ¼ 7.1, 14.2 Hz, 6H), 0.93 (dd, J ¼ 7.1, 13.1 Hz,
6H), 0.90 (dd, J ¼ 7.1, 11.0 Hz, 6H); 31P NMR (CDCl3):
h ¼ 26.0°; 3: d ¼ 7.32 A, r ¼ 3.68 A, h ¼ 33.0°; 4:
ꢀ
ꢀ
d ¼ 7.30 A, r ¼ 3.68 A, h ¼ 33.2°.
9. (S)-(4,40-Bi-1,3-benzodioxole)-5,50-diylbis(3,3-di-isopropyl-
phosphetane) (S)-1: Mp 68–70 °C; 1H NMR (CD2Cl2): d
6.98–6.94(m, 2H), 6.87 (d, J ¼ 7.7 Hz, 2H), 5.97 (d,
J ¼ 1.1 Hz, 2H), 5.84(d, J ¼ 1.1 Hz, 2H), 2.13–2.07 (m,
2H), 1.92–1.87 (m, 2H), 1.70 (dd, J ¼ 12.6, 23.1 Hz, 2H),
1.66 (dd, J ¼ 6.6, 6.6 Hz, 2H), 1.47 (dd, J ¼ 6.6, 6.6 Hz,
d ꢁ 3:0; CI-MS: m=z 475 (M)þ; ½aꢀ ¼ +6.5 (c 1.0, CHCl3).
D
13. Saito, T.; Yokozawa, T.; Zhang, X.; Sayo, N. U.S.
5,872,273, 1999.