2648
I. V. Paul Raj, A. Sudalai / Tetrahedron Letters 49 (2008) 2646–2648
OH
O
O
a
OH
Ph
Ph
Ph
+
( )-15
16 42%; 98% ee
17 46%; 94% ee
b
OR
OTBS
OTBS
e
d
CHO
Ph
Ph
Ph
OH
6 R= H
18 R= TBS
20
19
c
f
O
OH
O
O
O
g
Ph
OEt
Ph
OMe
94% ee
21
4
Scheme 3. Reagents and conditions: (a) (S,S)-Co(III)-salenꢁOAc (0.5 mol %), H2O (0.55 equiv), 25 °C; (b) (CH3)3S+Iꢀ, n-BuLi, THF, ꢀ10 °C, 82%; (c)
TBSCl, imidazole, CH2Cl2, 97%; (d) (i) Me2SꢁBH3, THF, (ii) 3 N NaOH, 30% H2O2,73%; (e) IBX, DMSO, 0 °C, 96%; (f) BF3ꢁOEt2, N2CHCO2Et,
CH2Cl2, ꢀ10 °C, 77%; (g) (i) K2CO3, MeOH, (ii) (CH3)2SO4, acetone, 81%.
6. (a) Kwon, T. W.; Keusenkothen, P. F.; Smith, M. B. J. Org. Chem.
epoxides 8 and 15, respectively. Hydrolytic kinetic resolu-
tion coupled with regiospecific ring opening of chiral epox-
1992, 57, 6169; (b) Wei, Z. Y.; Knaus, E. E. J. Org. Chem. 1993, 58,
1586; (c) Trost, B. M.; Lemoine, R. C. Tetrahedron Lett. 1996, 37,
ides with dimethylsulfonium methylide constituted the key
9161; (d) Alcon, M.; Poch, M.; Moyano, A.; Pericas, M. A.; Riera, A.
steps. Good yields, simple and ready availability of starting
Tetrahedron: Asymmetry 1997, 8, 2967; (e) Chandrasekhar, S.;
materials and less number of steps are some of the salient
features of this approach.
Mohapatra, S. Tetrahedron Lett. 1998, 39, 6415; (f) Masson, G.;
´
Zeghida, W.; Cividino, P.; Sandrine, Py.; Vallee, Y. Synlett 2003,
1527; (g) Anderson, C. E.; Overman, L. E. J. Am. Chem. Soc. 2003,
125, 12412; (h) Gheorghe, M.; Schulte, M.; Reiser, O. J. Org. Chem.
2006, 71, 2173.
Acknowledgements
7. (a) Smith, T. E.; Djang, M.; Velander, A. J.; Downey, C. W.; Carroll,
K. A.; van Alphen, S. Org. Lett. 2004, 6, 2317; (b) Wang, F.-D.; Yue,
J.-M. Eur. J. Org. Chem. 2005, 2575; (c) Sabitha, G.; Sudhakar, K.;
Yadav, J. S. Tetrahedron Lett. 2006, 47, 8599; (d) Spino, C.; Mayes,
One of the authors IVPR thanks CSIR, New Delhi, for
the award of research fellowship. The authors are also
thankful to Dr. B. D. Kulkarni, Head, CEPD, for his
support and encouragement.
´
N.; Desfosses, H. Tetrahedron Lett. 1996, 37, 6503; (e) Huck, W. R.;
Mallat, T.; Baiker, A. New J. Chem. 2002, 26, 6.
8. 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.
References and notes
9. (a) Alcaraz, L.; Harnett, J. J.; Mioskowski, C.; Martel, J. P.; LeGall,
T.; Shin, D.-S.; Falck, J. R. Tetrahedron Lett. 1994, 35, 5449; (b)
Baylon, C.; Heck, M.-P.; Mioskowski, C. J. Org. Chem. 1999, 64,
3354; (c) Davoille, R. J.; Rutherford, D. T.; Christie, S. D. R.
Tetrahedron Lett. 2000, 41, 1255.
1. (a) Lloyd, K. G.; Sheman, L.; Hornykiewicz, O. Brain Res. 1977, 127,
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Neurotransmitters; Munksgaard: Copenhagen, 1979; (c) Perry, T. L.;
Hansen, S.; Kloster, M. N. New Engl. J. Med. 1973, 288, 337; (d)
Perry, T. L.; Hansen, S.; Urquhart, N. Lancet 1974, 7, 996.
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Pharmacol. 1974, 23, 3053.
3. (a) Metcalf, B. W.; Casara, P. Tetrahedron Lett. 1975, 16, 3337; (b)
Metcalf, B.; Casara, P. J. Chem. Soc., Chem. Commun. 1979, 119; (c)
Casara, P. Tetrahedron Lett. 1994, 35, 3049.
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1977, 74, 441.
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Smith, K. K.; Dharmaratne, H. R. W.; Feltenstein, M. W.; Broom, S.
L.; Roach, J. T.; Nanayakkara, N. P. D.; Khan, I. A.; Sufka, K. J.
Psychopharmacology 2001, 155, 86; (c) Jamieson, D. D.; Duffield, P.
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11. Spectral data for 5: Colorless oil; IR (KBr): 669, 859, 1032, 1215,
1473, 1590, 3019 cmꢀ1; 1H NMR (200 MHz, CDCl3): d 1.57–1.70 (m,
4H), 3.42–3.48 (t, J = 5.4 Hz, 2H), 3.78 (s, 3H), 4.05–4.11 (m, 1H),
4.42 (s, 2H), 5.03–5.23 (m, 2H), 5.75–5.91 (m, 1H), 6.82–6.86 (d,
J = 8.7 Hz, 2H), 7.20–7.24 (d, J = 8.7 Hz, 2H); 13C NMR (50 MHz,
CDCl3): d 25.7, 34.3, 55.0, 69.9, 72.4, 72.5, 113.7, 114.2, 129.2, 130.1,
141.1, 159.1. Anal. Calcd for C14H20O3: C, 71.16; H, 8.53. Found: C,
71.27; H, 8.73.
25
12. Spectral data for 17: ½aꢂD ꢀ4.65 (c 1, CHCl3); 94% ee [Chiral OD-H
column; hexane/i-PrOH (98:2 v/v); flow rate 1.0 mL/min; UV
ꢀ210 nm; column temperature 25 °C; retention time: 13.295 min (R-
isomer) and 14.450 min (S-isomer)]; colorless liquid; IR (KBr): 821,
1035, 1247, 1514, 1614, 2339, 2856 cmꢀ1 1H NMR (200 MHz,
;
CDCl3): d 1.84–1.88 (m, 2H), 2.46–2.50 (m, 1H), 2.73–2.81 (m, 4H),
7.19–7.29 (m, 5H); 13C NMR (50 MHz, CDCl3): d 32.3, 34.3, 47.0,
51.5, 126.0, 128.3, 128.4, 141.1. Anal. Calcd for C10H12O: C, 81.04; H,
8.16. Found: C, 81.07; H, 8.13.