CLUSTER
Synthesis of 1,2,3-prim,sec,sec-Triols
3523
(10) For a-oxidations with nitrosobenzene, see: (a) Bøgevig, A.;
Sundén, H.; Córdova, A. Angew. Chem. Int. Ed. 2004, 43,
1109. (b) Córdova, A.; Sundén, H.; Bøgevig, A.; Johansson,
M.; Himo, F. Chem. Eur. J. 2004, 10, 3673. (c) Zhong, G.
Angew. Chem. Int. Ed. 2003, 42, 4247. (d) Brown, S. P.;
Brochu, M. P.; Sinz, C. J.; MacMillan, D. W. C. J. Am.
Chem. Soc. 2003, 125, 10808. (e) Hayashi, Y.; Yamaguchi,
J.; Hibino, K.; Shoji, M. Tetrahedron Lett. 2003, 44, 8293.
(f) Hayashi, Y.; Yamaguchi, J.; Hibino, K.; Shoji, M.
Angew. Chem. Int. Ed. 2004, 43, 1112. (g) Hayashi, Y.;
Yamaguchi, J.; Sumiya, T.; Hibino, K.; Shoji, M. J. Org.
Chem. 2004, 69, 5966. (h) Momiyama, N.; Torii, H.; Saito,
S.; Yamamoto, H. Proc. Natl. Acad. Sci. U.S.A. 2004, 101,
5374. (i) Yamamoto, Y.; Momiyama, N.; Yamamoto, H. J.
Am. Chem. Soc. 2004, 126, 5962. (j) Wang, W.; Wang, J.;
Li, H.; Liao, L. Tetrahedron Lett. 2004, 45, 7235. For a-
oxidations with singlet molecular oxygen, see: (k)Córdova,
A.; Sundén, H.; Engqvist, M.; Ibrahem, I.; Casas, J. J. Am.
Chem. Soc. 2004, 126, 8914. (l) Sundén, H.; Engqvist, M.;
Casas, J.; Ibrahem, I.; Córdova, A. Angew. Chem. Int. Ed.
2004, 43, 6532. (m) With other oxidants, see: Engqvist, M.;
Casas, J.; Sundén, H.; Ibrahem, I.; Córdova, A. Tetrahedron
Lett. 2005, 46, 2053.
Acknowledgment
We thank the Swedish National Research council and Carl-Trygger
Foundation for financial support.
References and Notes
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(12) To a stirred solution of 3 (16 mg, 20 mol%) in CHCl3 (2 mL)
was added trans-cinnamaldehyde (1a, 66 mg, 0.5 mmol) and
H2O2 (0.6 mmol, 50% aq solution). The reaction was
vigorously stirred at 4 °C for 7 h. Then the reaction mixture
was diluted with EtOH (2 mL) and cooled to 0 °C followed
by addition of NaBH4 (38 mg, 1.0 mmol). The mixture was
then stirred for 10 min, quenched with H2SO4 (0.5 N, 8 mL)
and EtOAc (8 mL). Next, the reaction mixture was stirred at
r.t. for 1 h. The mixture was separated and the water layer
was extracted with EtOAc (6 × 5 mL). The organic layer was
collected, dried over Na2SO4 and the solvent was removed.
The residue was purified by silica gel chromatography
(EtOAc) to give the product 2a (53 mg, 63%).
(6) (a) Katsuki, T.; Lee, A. W. M.; Ma, P.; Martin, V. S.;
Masamune, S.; Sharpless, K. B.; Tuddenham, D.; Walker, F.
J. J. Org. Chem. 1982, 47, 1378. (b) Ko, S. Y.; Lee, A. W.
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Lett. 1994, 35, 843. (b) Xu, D.; Park, C. Y.; Sharpless, K. B.
Tetrahedron Lett. 1994, 35, 2495. (c) Lohray, B. B.;
Kalantar, T. H.; Kim, B. M.; Park, C. Y.; Shibata, T.; Wai, J.
S. M.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 2041.
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5138. (b) Merino, P.; Tejero, T. Angew. Chem. Int. Ed. 2004,
43, 2995. (c) Armstrong, A. Angew. Chem. Int. Ed. 2004, 43,
1460. (d) Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed.
2001, 40, 3726. (e) List, B. Tetrahedron 2002, 58, 5573.
(f) Duthaler, R. O. Angew. Chem. Int. Ed. 2003, 42, 975.
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(a) Julía, S.; Masana, J.; Vega, J. C. Angew. Chem., Int. Ed.
Engl. 1980, 19, 929. (b) Julía, S.; Guixer, J.; Masana, J.;
Rocas, J.; Colonna, S.; Annunziata, R.; Molinari, H. J.
Chem. Soc., Perkin Trans. 1 1982, 1317. (c) Helder, T.;
Hummelen, J. C.; Laane, R. W. P. M.; Wiering, J. S.;
Wynberg, H. Tetrahedron Lett. 1976, 1831. (d)Corey, E. J.;
Zhang, F.-Y. Org. Lett. 1999, 1, 1287. (e) Lygo, B.;
Wainwright, P. G. Tetrahedron Lett. 1998, 38, 1599.
(f) Jew, S.-S.; Lee, J.-H.; Jeong, B.-S.; Yoo, M.-S.; Kim, M.-
J.; Lee, Y.-J.; Lee, J.; Choi, S.-H.; Lee, K.; Lah, M.-S.; Park,
H.-G. Angew. Chem. Int. Ed. 2005, 44, 1383. (g) For the
use of chiral ketones as catalysts, see: Shi, Y. Acc. Chem.
Res. 2004, 37, 488; and references therein. (h) For the use
of chiral amines, see: Bohe, L.; Hanquet, M.; Lusinchi, M.;
Lusinchi, X. Tetrahedron Lett. 1993, 34, 7271. (i) Adamo,
M. F. A.; Aggarwal, V. K.; Sage, M. A. J. Am. Chem. Soc.
2000, 122, 8317. (j) Lattanzi, A. Org. Lett. 2005, 7, 2579.
(k) Lattanzi, A. Adv. Synth. Catal. 2006, 7, 339.
(2R,3S)-1-Phenyl-propane-1,2,3-triol (2a): [a]D25 +30.3 (c
1.0, CHCl3); [a]D25 +25.3 (c 1.0, H2O), lit.4a [a]D23 +19.6 (c
6.3, H2O). 1H NMR (400 MHz, D2O): d (major
diastereomer) = 3.64 (dd, J = 7.2, 11.6 Hz, 1 H), 3.82 (dd,
J = 3.2, 11.6 Hz, 1 H), 3.94 (ddd, J = 3.2, 7.2, 7.2 Hz, 1 H),
4.67 (d, J = 7.2 Hz, 1 H), 7.41–7.49 (m, 5 H); d (minor
diastereomer) = 3.43 (dd, J = 7.2, 12.0 Hz, 1 H), 3.54 (dd,
J = 4.0, 12.0 Hz, 1 H), 3.89 (ddd, J = 4.0, 6.4, 7.2 Hz, 1 H),
4.70 (d, J = 6.4 Hz, 1 H), 7.41–7.49 (m, 5 H). 13C NMR (100
MHz, D2O): d (major isomer) = 62.8. 74.1, 74.8, 127.4,
128.4, 128.8, 140.6; d (minor isomer) = 62.7. 74.4, 75.7,
126.9, 128.4, 128.9, 140.7. The ee was determined after
acetylation by HPLC on Daicel Chiralpak OJ with iso-
hexane–i-PrOH (85:15) as the eluent; major diastereomer –
minor isomer: tR = 20.923 min; major isomer: tR = 28.299
min; minor diastereomer – minor isomer: tR = 36.090 min;
major isomer: tR = 49.281 min. HRMS (ESI): m/z calcd for
C9H12O3Na [M + Na]+: 191.0679; found: 191.0687.
(13) To a stirred solution of 3 (16 mg, 20 mol%) in CHCl3 (2 mL)
was added trans-cinnamaldehyde (1a, 66 mg, 0.5 mmol) and
H2O2 (0.6 mmol, 50% aq solution). The reaction was
vigorously stirred at 4 °C for 7 h. Then the reaction mixture
was diluted with EtOH (2 mL) and cooled to 0 °C followed
by addition of NaBH4 (38 mg, 1.0 mmol) and the mixture
was stirred for 10 min. Next, NaOH (0.5 N, 10 mL) and
t-BuOH (2 mL) were added and the reaction temperature
Synlett 2006, No. 20, 3521–3524 © Thieme Stuttgart · New York