Highly diastereoselective samarium-Reformatsky reaction of chiral α- bromoacetyl-2-oxazolidinones with aldehydes

Tetrahedron Letters

Volumn 39, Issue 38, 1998, Pages 6899-6900

  Fukuzawa, Shin Ichi ^a   Tatsuzawa, Masahiro ^a   Hirano, Kohki ^a  

^a CHUO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE; ALDEHYDE DERIVATIVE; BROMOACETIC ACID; SAMARIUM; TETRAHYDROFURAN;

ARTICLE; CHELATION; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032541685     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01446-4     Document Type: Article

References (16)

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5. (d) Kawatsura, M.; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett, 1996, 373.
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11. (5) Zinc promoted Reformasky reaction with α-bromoacetyl-2-oxazolidinone has been studied, but only one experimental result are reported. Ito, Y.; Terashima, S. Tetrahedron, 1991, 47, 2821.
12. (6) Diastereoselective intramolecular samarium-Reformatsky reaction has been reported. Molander G. A.; Etter, J. B.; Harring, L. S.; Thorel, P.-J. J. Am. Chem. Soc. 1992, 114, 1656.
13. (7) Evans, D.A.; Bartroli, J.; Shih, T.L. J. Am. Chem. Soc. 1981, 114, 2127.
14. (8) (a) Sugiura, T.; Yoshikawa, M.; Yoneda, T.; Tai, A. Bull. Chem. Soc. Jpn. 1990, 63, 1080.
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16. (c) Soai, K.; Yamanoi, T.; Hikima, H.; Oyamada, H. Chem. Commun. 1985, 138.