Asymmetric synthesis of the 4-hydroxymethyl-2-oxazolidinone from the serinol derivative and chloroformates

Tetrahedron Letters

Volumn 40, Issue 42, 1999, Pages 7489-7492

  Sugiyama, Shigeo ^a   Watanabe, Shoko ^a   Ishii, Keitaro ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Amino alcohols; Cyclization; Diastereoselection; Oxazolidinones

Indexed keywords

AMINOALCOHOL; CHLOROFORM; FORMIC ACID DERIVATIVE; OXAZOLIDINONE DERIVATIVE; SERINE DERIVATIVE;

ARTICLE; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033569867     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01548-8     Document Type: Article

References (18)

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8. (a) Sibi, M. P.; Renhowe, P. A. Tetrahedron Lett. 1990, 31, 7407-7410. (b) Sibi, M. P.; Li, B. Tetrahedron Lett. 1992, 33, 4115-4118. (c) Sibi, M. P.; Christensen, J. W.; Li, B.; Renhowe, P. A. J. Org. Chem. 1992, 57, 4329-4330. (d) Sibi, M. P.; Rutherford, D.; Sharma, R. J. Chem. Soc., Perkin Trans. 1 1994, 1675-1678. (e) Sibi, M. P.; Harris, B. J.; Shay, J. J.; Hajra, S. Tetrahedron 1998, 54, 7221-7228. (f) Katsumura, S.; Yamamoto, N.; Morita, M.; Han, Q. Tetrahedron: Asymmetry 1994, 5, 161-164. (g) Iwama, S.; Katsumura, S. Bull. Chem. Soc. Jpn. 1994, 67, 3363-3365. (h) Katsumura, S.; Yamamoto, N.; Fukuda, E.; Iwama, S. Chem. Lett. 1995, 393-394. (i) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418-5424.
9. (a) Sibi, M. P.; Renhowe, P. A. Tetrahedron Lett. 1990, 31, 7407-7410. (b) Sibi, M. P.; Li, B. Tetrahedron Lett. 1992, 33, 4115-4118. (c) Sibi, M. P.; Christensen, J. W.; Li, B.; Renhowe, P. A. J. Org. Chem. 1992, 57, 4329-4330. (d) Sibi, M. P.; Rutherford, D.; Sharma, R. J. Chem. Soc., Perkin Trans. 1 1994, 1675-1678. (e) Sibi, M. P.; Harris, B. J.; Shay, J. J.; Hajra, S. Tetrahedron 1998, 54, 7221-7228. (f) Katsumura, S.; Yamamoto, N.; Morita, M.; Han, Q. Tetrahedron: Asymmetry 1994, 5, 161-164. (g) Iwama, S.; Katsumura, S. Bull. Chem. Soc. Jpn. 1994, 67, 3363-3365. (h) Katsumura, S.; Yamamoto, N.; Fukuda, E.; Iwama, S. Chem. Lett. 1995, 393-394. (i) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418-5424.
10. (a) Sibi, M. P.; Renhowe, P. A. Tetrahedron Lett. 1990, 31, 7407-7410. (b) Sibi, M. P.; Li, B. Tetrahedron Lett. 1992, 33, 4115-4118. (c) Sibi, M. P.; Christensen, J. W.; Li, B.; Renhowe, P. A. J. Org. Chem. 1992, 57, 4329-4330. (d) Sibi, M. P.; Rutherford, D.; Sharma, R. J. Chem. Soc., Perkin Trans. 1 1994, 1675-1678. (e) Sibi, M. P.; Harris, B. J.; Shay, J. J.; Hajra, S. Tetrahedron 1998, 54, 7221-7228. (f) Katsumura, S.; Yamamoto, N.; Morita, M.; Han, Q. Tetrahedron: Asymmetry 1994, 5, 161-164. (g) Iwama, S.; Katsumura, S. Bull. Chem. Soc. Jpn. 1994, 67, 3363-3365. (h) Katsumura, S.; Yamamoto, N.; Fukuda, E.; Iwama, S. Chem. Lett. 1995, 393-394. (i) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418-5424.
11. (a) Sibi, M. P.; Renhowe, P. A. Tetrahedron Lett. 1990, 31, 7407-7410. (b) Sibi, M. P.; Li, B. Tetrahedron Lett. 1992, 33, 4115-4118. (c) Sibi, M. P.; Christensen, J. W.; Li, B.; Renhowe, P. A. J. Org. Chem. 1992, 57, 4329-4330. (d) Sibi, M. P.; Rutherford, D.; Sharma, R. J. Chem. Soc., Perkin Trans. 1 1994, 1675-1678. (e) Sibi, M. P.; Harris, B. J.; Shay, J. J.; Hajra, S. Tetrahedron 1998, 54, 7221-7228. (f) Katsumura, S.; Yamamoto, N.; Morita, M.; Han, Q. Tetrahedron: Asymmetry 1994, 5, 161-164. (g) Iwama, S.; Katsumura, S. Bull. Chem. Soc. Jpn. 1994, 67, 3363-3365. (h) Katsumura, S.; Yamamoto, N.; Fukuda, E.; Iwama, S. Chem. Lett. 1995, 393-394. (i) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418-5424.
12. (a) Sibi, M. P.; Renhowe, P. A. Tetrahedron Lett. 1990, 31, 7407-7410. (b) Sibi, M. P.; Li, B. Tetrahedron Lett. 1992, 33, 4115-4118. (c) Sibi, M. P.; Christensen, J. W.; Li, B.; Renhowe, P. A. J. Org. Chem. 1992, 57, 4329-4330. (d) Sibi, M. P.; Rutherford, D.; Sharma, R. J. Chem. Soc., Perkin Trans. 1 1994, 1675-1678. (e) Sibi, M. P.; Harris, B. J.; Shay, J. J.; Hajra, S. Tetrahedron 1998, 54, 7221-7228. (f) Katsumura, S.; Yamamoto, N.; Morita, M.; Han, Q. Tetrahedron: Asymmetry 1994, 5, 161-164. (g) Iwama, S.; Katsumura, S. Bull. Chem. Soc. Jpn. 1994, 67, 3363-3365. (h) Katsumura, S.; Yamamoto, N.; Fukuda, E.; Iwama, S. Chem. Lett. 1995, 393-394. (i) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418-5424.
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17. 4
18. The procedure is as follows. Serinol 1 (5.00 g, 25.6 mmol) was dissolved in methylene chloride (640 mL, 0.04 mol/L) at 40°C (bath temperature). Pyridine (2.16 g, 25.6 mmol) was added, and then 2-chloroethyl chloroformate (3.66 g, 25.6 mmol) was added by one shot to the mixture at room temperature. After being stirred for 24 h at room temperature, the mixture was cooled to 1°C (internal temperature) with an ice bath and treated with DBU (11.85 g, 76.8 mmol). The resulting mixture was stirred for 4 h with warming to room temperature. The reaction mixture was washed twice with 5% HCl aq. (60 mL) and once with water (60 mL). It was then dried, filtered and concentrated in vacuo to give a yellow oil (5.92 g) which was chromatographed on silica gel (hexane:AcOEt 1:2, column 7 cm Φ×22 cm) to afford biscarbonate 3 (503 mg, 5%) as a colorless oil and a mixture of oxazolidinones (4S)-2 and (4R)-2 (3.85 g, 68% yield, 97: 3, 94% de) as colorless crystals. The crystals (3.84 g) were recrystallized from tert-butyl methyl ether (30 mL) to give pure (4S)-2 as colorless plates (2.19 g).