A study of 4-substituted 5,5-diaryl oxazolidin-2-ones as efficacious chiral auxiliaries

Tetrahedron Letters

Volumn 39, Issue 37, 1998, Pages 6733-6736

  Gibson, Colin L ^a   Gillon, Karen ^a   Cook, Stuart ^b  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b Hickson and Welch Ltd   (United Kingdom)

Author keywords

Asymmetric synthesis; Diastereoselection; Oxazolidinones

Indexed keywords

5,5 DIARYL OXAZOLIDIN 2 ONE; UNCLASSIFIED DRUG;

ALKYLATION; AMINATION; ARTICLE; BROMINATION; CHIRALITY; DIASTEREOISOMER; HYDROLYSIS; HYDROXYLATION; METHODOLOGY; STEREOCHEMISTRY;

EID: 0032505206     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01412-9     Document Type: Article

References (15)

1. [1] For reviews of the use of oxazolidin-2-ones as chiral auxiliaries see: Ager, D. J.; Prakash, J.; Schaad, D. R. Aldrichimica Acta, 1997, 30, 3. Ager, D. J.; Prakash, J.; Schaad, D. R. Chem. Rev., 1996, 96, 835. Evans, D. A. Aldrichimica Acta, 1982, 15, 23.
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3. [1] For reviews of the use of oxazolidin-2-ones as chiral auxiliaries see: Ager, D. J.; Prakash, J.; Schaad, D. R. Aldrichimica Acta, 1997, 30, 3. Ager, D. J.; Prakash, J.; Schaad, D. R. Chem. Rev., 1996, 96, 835. Evans, D. A. Aldrichimica Acta, 1982, 15, 23.
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6. [3] Davies, S. G.; Sanganee, H. J. Tetrahedron: Asymmetry, 1995, 6, 671. Bull, S. G.; Davies, S. G.; Jones, S.; Polywka, M. E. C.; Prasad, R. S.; Sanganee, H. J. Synlett, 1998, 519.
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8. [4] Delair, P.; Einhorn, C.; Luche, J. J. Org. Chem., 1994, 59, 4680. Delaunay, D., Le Corre, M. Chem. Comm., 1994, 3041. Cardillo, G.; Gentilucci, L.; Tomasini, C.; Tomasoni, L., Tetrahedron: Asymmetry, 1995, 6, 1947.
9. [4] Delair, P.; Einhorn, C.; Luche, J. J. Org. Chem., 1994, 59, 4680. Delaunay, D., Le Corre, M. Chem. Comm., 1994, 3041. Cardillo, G.; Gentilucci, L.; Tomasini, C.; Tomasoni, L., Tetrahedron: Asymmetry, 1995, 6, 1947.
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12. 13C nmr, accurate mass and/or elemental analysis.
13. [7] The 5,5-diaryl oxazolidin-2-ones 2a-c are now commercially available from Hickson & Welch Ltd.
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15. [9] Parker, D.; Fulwood, R. Tetrahedron: Asymmetry, 1992, 3, 25.