Shao, Shen & Ye
FULL PAPER
65.8 mg (70%). White solid, m.p. 123—125 ℃; Rf=
0.15 (petroleum ether/ethyl acetate, V∶V=2∶1);
[α]2D0 -64.3 (c 1.1, MeOH) [Ref:[17] [α]2D0 -76.8 (c
31.8, 29.4, 25.6, 22.7, 14.1; HPLC analysis of its
dibenzoate derivative: 86% ee [Daicel CHIRALPAK
AD-H column, 20 ℃, 254 nm, 1.0 mL/min, solvent
system: 2-propanol/hexane, V∶V=5∶95; retention
times: 12.7 min (minor), 16.4 min (major)].
1
1.0, MeOH)]; H NMR (300 MHz, CDCl3) δ: 8.10—
8.05 (m, 1H), 7.90—7.80 (m, 2H), 7.72—7.70 (m, 1H),
7.56—7.47 (m, 3H), 5.64 (d, J=5.7 Hz, 1H), 4.01—
3.97 (m, 1H), 3.83—3.76 (m, 1H), 2.66 (br s, 1H), 2.21
(br s, 1H); 13C NMR (75 MHz,CDCl3) δ: 136.0, 133.6,
130.3, 128.9, 128.3, 126.3, 125.6, 125.4, 123.5, 122.6,
71.6, 67.5; HPLC analysis: 97% ee [Daicel
CHIRALPAK OD-H column; 20 ℃, 210 nm, 1.0
mL/min; solvent system: 2-propanol/hexane, V∶V=
10∶90; retention times: 13.4 min (major), 23.6 min
(minor)].
Acknowledgement
This work was supported by the National Natural
Science Foundation of China (No. 21072195) and the
Major State Basic Research Development Program (No.
2011CB808600).
References
(R)-1-(Naphthalen-2-yl)ethane-1,2-diol (4h): Yield
64.9 mg (69%). White solid, m.p. 136—138 ℃; Rf=
0.15 (petroleum ether/ethyl acetate, V∶V=2∶1).
[α]2D0 -42.6 (c 1.4, EtOH) [Ref:[18] [α]2D3 -31.2 (c
[1] (a) Hanessian, H. Total Synthesis of Natural Products: The “Chiron”
Approach, Pergamon, Oxford, 1983; (b) Bianchi, D.; Bosetti, A.;
Cesti, P.; Golini, P. Tetrahedron Lett. 1992, 33, 3231; (c) Wang,
Z.-M.; Zhang, X.-L.; Sharpless, K. B. Tetrahedron Lett. 1993, 34,
2267; (d) Fürstner, A.; Bogdanović, B. Angew. Chem., Int. Ed. 1996,
35, 2442; (e) Cho, B. T.; Chun, Y. S. Tetrahedron: Asymmetry 1999,
10, 1843; (f) Duchek, J.; Adams, D. R.; Hudlicky, T. Chem. Rev.
2011, 111, 4223.
[2] (a) Schmidt, M.; Amstutz, R.; Crass, G.; Seebach, D. Chem. Ber.
1980, 113, 1691; (b) Kagan, H. B.; Dang, T.-P. J. Am. Chem. Soc.
1972, 94, 6429; (c) Hoffmann, R. W. Pure. Appl. Chem. 1988, 60,
123; (d) Hasegawa, K.; Matsuda, F.; Yanagiya, M.; Matsumoto, T.
Tetrahedron Lett. 1987, 28, 1671; (e) Narasaka, K.; Iwasawa, N.;
Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem.
Soc. 1989, 111, 5345; (f) Kang, S. H.; Jeong, J. W.; Hwang, Y. S.;
Lee, S. B. Angew. Chem., Int. Ed. 2002, 41, 1392; (g) Smith III, A.
B.; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J.
Am. Chem. Soc. 1995, 117, 12013; (h) Haukaas, M. H.; O’Doherty,
G. A. Org. Lett. 2002, 4, 1771.
[3] (a) Choi, D. S.; Han, S. S.; Kwueon, E. K.; Choi, H. Y.; Hwang, S.
H.; Park, Y. S.; Song, C. E. Adv. Synth. Catal. 2006, 348, 2560;
(b) Jin, Y.; Yao, Z.-J.; Zhang, S.-Y.; Jiang, R.; Sun, X.-L. Chin. J.
Org. Chem. 2007, 27, 602 (in Chinese); (c) Liu, W.-M.; Liu, X.-Y.;
Song, R.-J.; Zhang, S.-Y. Chin. J. Org. Chem. 2006, 26, 341 (in
Chinese).
[4] (a) Palucki, M.; Pospisil, P. J.; Zhang, W.; Jacobsen, E. N. J. Am.
Chem. Soc. 1994, 116, 9333; (b) Collman, J. P.; Wang, Z.;
Straumanis, A.; Quelquejeu, M.; Rose, E. J. Am. Chem. Soc. 1999,
121, 460; (c) Botes, A. L.; Weijers, C. A. G. M.; Botes, P. J.; van
Dyk, M. S. Tetrahedron: Asymmetry 1999, 10, 3327; (d) Goswami,
A.; Totleben, M. J.; Singh, A. K.; Patel, R. N. Tetrahedron: Asym-
metry 1999, 10, 3167.
1
0.997, EtOH)]; H NMR (300 MHz, (CD3)2CO) δ:
7.90—7.84 (m, 4H), 7.57—7.45 (m, 3H), 4.89 (dd, J=
3.9, 7.7 Hz, 1H), 4.45 (d, J=3.7 Hz, 1H), 3.88—3.84
(m, 1H), 3.78—3.68 (m, 1H), 3.66—3.60 (m, 1H); 13C
NMR (75 MHz, (CD3)2CO) δ: 141.3, 134.3, 133.9,
128.7, 128.4, 128.4, 126.7, 126.4, 125.7, 125.6, 75.4,
68.9; HPLC analysis: 98% ee [Daicel CHIRALPAK
OD-H column; 20 ℃, 210 nm, 1.0 mL/min; solvent
system: 2-propanol/hexane, V∶V=10∶90; retention
times: 15.2 min (major), 19.2 min (minor)].
(R)-3-Phenylpropane-1,2-diol (4i): Yield 35.7 mg
(47%). Colorless oil; Rf=0.15 (petroleum ether/ethyl
acetate, V∶V=2∶1); [α]2D0 18.5 (c 0.5, EtOH) [Ref:[8]
[α]2D0 25.5 (c 1.0, EtOH)]; 1H NMR (300 MHz, CDCl3)
δ: 7.35—7.21 (m, 5H), 4.00—3.92 (m, 1H), 3.70 (dd,
J=3.2, 11.1 Hz, 1H), 3.53 (dd, J=7.0, 11.1 Hz, 1H),
2.85—2.71 (m, 2H), 2.04 (br s, 2H); 13C NMR (75 MHz,
CDCl3) δ: 137.8, 129.4, 128.7, 126.7, 73.1, 66.1, 39.8;
HPLC analysis: 99% ee [Daicel CHIRALPAK OD-H
column; 20 ℃, 210 nm, 1.0 mL/min; solvent system:
2-propanol/hexane, V∶V=5∶95; retention times: 18.9
min (major), 20.7 (minor)].
(R)-Butane-1,2-diol (4j): Yield 25.2 mg (56%). Col-
orless oil; Rf=0.15 (petroleum ether/ethyl acetate, V∶V
=2∶1). [α]2D0 12.0 (c 0.1, EtOH) [Ref:[19] [α]D20 15.0
(c 1.7, EtOH)]; 1H NMR (300 MHz, CDCl3) δ: 3.90 (br
s, 2H), 3.64—3.61 (m, 2H), 3.45—3.38 (m, 1H), 1.50—
1.41 (m, 2H), 0.96 (t, J=7.5 Hz, 3H); 13C NMR (75
MHz, CDCl3) δ: 73.8, 66.4, 26.0, 9.9; GC analysis of its
bistrifluoroacetate derivative: 75% ee [CHIRALDEX
G-TA column, 30 m×0.25 mm×0.12 μm, 7 psi, 60 ℃,
2 min, 1 ℃/min, retention times: 11.6 min (major),
11.9 min (minor)].
[5] Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen,
K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem.
Soc. 2002, 124, 1307.
[6] Xu, Y.; Jia, X.; Panke, S.; Li, Z. Chem. Commun. 2009, 1481.
[7] (a) Ohkuma, T.; Utsumi, N.; Watanabe, M.; Tsutsumi, K.; Arai, N.;
Murata, K. Org. Lett. 2007, 9, 2565; (b) Kadyrov, R.; Koenigs, R.
M.; Brinkmann, C.; Voigtlaender, D.; Rueping, M. Angew. Chem.,
Int. Ed. 2009, 48, 7556; (c) Touge, T.; Hakamata, T.; Nara, H.; Ko-
bayashi, T.; Sayo, N.; Saito, T.; Kayaki, Y.; Ikariya, T. J. Am. Chem.
Soc. 2011, 133, 14960; (d) Xu, H.; Meng, Q.-H.; Zhang, Z.-G. Chin.
J. Chem. 2008, 26, 1656.
(R)-Octane-1,2-diol (4k): Yield 37.9 mg (52%).
Colorless oil; Rf=0.15 (petroleum ether/ethyl acetate,
V∶V=2∶1). [α]2D0 13.6 (c 1.2, MeOH) [Ref:[20]
[8] Brown, S. P.; Brochu, M. P.; Sinz, C. J.; MacMillan, D. W. C. J. Am.
Chem. Soc. 2003, 125, 10808.
[9] (a) Zhu, C.; Shen, X.; Nelson, S. G. J. Am. Chem. Soc. 2004, 126,
5352; (b) Chandra, B.; Fu, D.; Nelson, S. G. Angew. Chem., Int. Ed.
2010, 49, 2591; (c) Vargo, T. R.; Hale, J. S.; Nelson, S. G. Angew.
Chem., Int. Ed. 2010, 49, 8678; (d) Xu, X.; Wang, K.; Nelson, S. G.
J. Am. Chem. Soc. 2007, 129, 11690; (e) Tseni, P. S.; Peters, R.
1
[α]2D4 +12.8 (c 0.95, MeOH)], H NMR (300 MHz,
CDCl3) δ: 3.67—3.62 (m, 2H), 3.44—3.38 (m, 1H),
2.80 (br s, 2H), 1.42—1.28 (m, 10H), 0.86 (t, J=6.6 Hz,
3H); 13C NMR (75 MHz, CDCl3) δ: 72.4, 66.9, 33.2,
4
© 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2012, XX, 1—5