Stereoselective gram-scale synthesis of (S)-5,5-dimethyl-4-phenyloxazolidin-2-one

Heterocycles

Volumn 65, Issue 1, 2005, Pages 149-159

  Sugiyama, Shigeo ^a   Arai, Satoshi ^a   Ishii, Keitaro ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33645601554     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-04-10220     Document Type: Article

References (24)

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19. Boyd D.R., Jennings W.B., and Waring L.C. J. Org. Chem. 51 (1986) 992
20. For NMR analysis of the minor oxazolidin-2-ones (7) and (12) we measured a mixture of oxazolidin-2-ones (3/7) (53:47) and 17/12 (70:30) obtained from the filtrate of the final recrystallization of 3 and 17, respectively.
21. 2 Davies and co-workers reported the synthesis of (S)-1 from N-Boc-l-phenylglycine methyl ester in 81% yield.
22. 23 We used this yield for the calculation of overall yield of (R)-1 from d-phenylglycine.
23. Yuste F., Ortiz B., Carrasco A., Peralta M., Quintero L., Sanchez-Obregon R., Walls F., and Ruano J.L.G. Tetrahededron: Asymmetry 11 (2000) 3079
24. Very recently, we have shown that this empirical rule is applicable to the interemediates of (-)- and (+)-cytoxazones. See:. Sugiyama S., Arai S., and Ishii K. Tetrahedron: Asymmetry 15 (2004) 3149