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Volumn 59, Issue 19, 2003, Pages 3417-3425

A novel dynamic kinetic resolution accompanied by intramolecular transesterification: Asymmetric synthesis of a 4-hydroxymethyl-2-oxazolidinone from serinol derivatives

Author keywords

Dynamic kinetic resolution; Oxazolidinone; Serinol; Transesterification

Indexed keywords

2 (ALPHA METHYLBENZYL)AMINO 1,3 PROPANEDIOL; 2 CHLOROETHYL 3 HYDROXY 2 (ALPHA METHYLBENZYL)AMINOPROPYLCARBONIC ACID; 2 CHLOROETHYLCHLOROFORMATE; 4 HYDROXYMETHYL 3 (ALPHA METHYLBENZYL) 2 OXAZOLIDINONE; CARBONIC ACID DERIVATIVE; DICHLOROMETHANE; FORMIC ACID DERIVATIVE; OXAZOLIDINONE DERIVATIVE; PROPANEDIOL DERIVATIVE; SERINE DERIVATIVE; SERINOL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037420839     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00477-0     Document Type: Article
Times cited : (20)

References (27)
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    • For reviews of DKR, see (a) Noyori R., Ohkuma T. Angew. Chem., Int. Ed. Engl. 40:2001;40-73 (b) Huerta F.F., Minidis A.B.E., Baeckvall J.-E. Chem. Soc. Rev. 30:2001;321-331 (c) Bringmann G., Menche D. Acc. Chem. Res. 34:2001;615-624 (d) Ratovelomanana-Vidal V., Genet J.-P. Can. J. Chem. 78:2000;846-851 (e) Beak P., Anderson D.R., Curtis M.D., Laumer J.M., Pippel D.J., Weisenburger G.A. Acc. Chem. Res. 33:2000;715-727 (f) Stecher H., Faber K. Synthesis. 1997;1-16 (g) Sturmer R. Angew. Chem., Int. Ed. Engl. 36:1997;1173-1174 (h) Caddick S., Jenkins K. Chem. Soc. Rev. 25:1996;447-456 (i) Ward R.S. Tetrahedron: Asymmetry. 6:1995;1475-1490 (j) Noyori R., Tokunaga M., Kitamura M. Bull. Chem. Soc. Jpn. 68:1995;36-56.
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    • Recent mechanistic studies for DKR, see (a) Santos A.G., Candeias S.X., Afonso C.A.M., Jenkins K., Caddick S., Treweeke N.R., Pardoe D. Tetrahedron. 57:2001;6607-6614 (b) Ben R.N., Durst T. J. Org. Chem. 64:1999;7700-7706 (c) Weisenburger G.A., Faibish N.C., Pippel D.J., Beak P. J. Am. Chem. Soc. 121:1999;9522-9530 (d) Tunge J.A., Gately D.A., Norton J.R. J. Am. Chem. Soc. 121:1999;4520-4521.
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    • Santos, A.G.1    Candeias, S.X.2    Afonso, C.A.M.3    Jenkins, K.4    Caddick, S.5    Treweeke, N.R.6    Pardoe, D.7
  • 12
    • 0032722407 scopus 로고    scopus 로고
    • Recent mechanistic studies for DKR, see (a) Santos A.G., Candeias S.X., Afonso C.A.M., Jenkins K., Caddick S., Treweeke N.R., Pardoe D. Tetrahedron. 57:2001;6607-6614 (b) Ben R.N., Durst T. J. Org. Chem. 64:1999;7700-7706 (c) Weisenburger G.A., Faibish N.C., Pippel D.J., Beak P. J. Am. Chem. Soc. 121:1999;9522-9530 (d) Tunge J.A., Gately D.A., Norton J.R. J. Am. Chem. Soc. 121:1999;4520-4521.
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    • Ben, R.N.1    Durst, T.2
  • 13
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    • Recent mechanistic studies for DKR, see (a) Santos A.G., Candeias S.X., Afonso C.A.M., Jenkins K., Caddick S., Treweeke N.R., Pardoe D. Tetrahedron. 57:2001;6607-6614 (b) Ben R.N., Durst T. J. Org. Chem. 64:1999;7700-7706 (c) Weisenburger G.A., Faibish N.C., Pippel D.J., Beak P. J. Am. Chem. Soc. 121:1999;9522-9530 (d) Tunge J.A., Gately D.A., Norton J.R. J. Am. Chem. Soc. 121:1999;4520-4521.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 9522-9530
    • Weisenburger, G.A.1    Faibish, N.C.2    Pippel, D.J.3    Beak, P.4
  • 14
    • 0033549046 scopus 로고    scopus 로고
    • Recent mechanistic studies for DKR, see (a)
    • Recent mechanistic studies for DKR, see (a) Santos A.G., Candeias S.X., Afonso C.A.M., Jenkins K., Caddick S., Treweeke N.R., Pardoe D. Tetrahedron. 57:2001;6607-6614 (b) Ben R.N., Durst T. J. Org. Chem. 64:1999;7700-7706 (c) Weisenburger G.A., Faibish N.C., Pippel D.J., Beak P. J. Am. Chem. Soc. 121:1999;9522-9530 (d) Tunge J.A., Gately D.A., Norton J.R. J. Am. Chem. Soc. 121:1999;4520-4521.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 4520-4521
    • Tunge, J.A.1    Gately, D.A.2    Norton, J.R.3


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