Asymmetric synthesis of chiral 4-substituted 5,5-diethyl oxazolidin-2-ones as potential effective chiral auxiliaries

Journal of Peptide Research

Volumn 66, Issue 6, 2005, Pages 319-323

  Li, J F ^a,b   Yang, R ^a   Nie, L ^a   Yang, L J ^c   Huang, R ^a   Lin, J ^a,b  

^a YUNNAN UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

^c YUNNAN MINZU UNIVERSITY   (China)

Author keywords

Aromatic amino acids; Asymmetric synthesis; Chiral auxiliary; Oxazolidinone

Indexed keywords

AMINO ACID; OXAZOLIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; ETHERIFICATION; PRIORITY JOURNAL; SYNTHESIS;

CYCLIZATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXAZOLIDINONES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 28944442159     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.2005.00310.x     Document Type: Article

References (17)

1. Evans, D.A., Bartroli, J. & Shih, T.L. (1981) Enantioselective aldol condensations. Erythro-selective chiral aldol condensations via boron enolates. J. Am. Chem. Soc. 103, 2127.
2. Ager, D.A., Prakash, J. & Schaad, D.R. (1997) Practical synthesis of α-amino alcohols via asymmetric catalytic hydrogenation. Aldrichim Acta 30, 3.
3. Ager, D.J., Prakash, J. & Schaad, D.R. (1996) 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis. Chem. Rev. 96, 835.
4. Evans, D.A. (1982) Studies in asymmetric synthesis. The development of practical chiral enolate synthons. Aldrichim Acta 15, 23.
5. Qian, X., Russell, K.C., Boteju, L.W. & Hruby, V.J. (1995) Stereoselective total synthesis of topographically constrained designer amino acids: 2′,6′-dimethyl-β-methyltyrosines. Tetrahedron 51, 1033-1054.
6. Liao, S. & Hruby, V.J. (1996) Asymmetric synthesis of optically pure β-isopropylphenylalanine: a new β-branched unusual amino acid. Tetrahedron Lett. 37, 1563-1566.
7. Yuan, W. & Hruby, V.J. (1997) Asymmetric synthesis of unusual amino acid: synthesis of four isomers of β-methyl-3-(2′-naphthyl)alanine. Tetrahedron Lett. 38, 3853-3856.
8. Lin, J., Liao, S., Han, Y.L., Qiu, W. & Hruby, V.J. (1997) Asymmetric synthesis of all four isomers of topographically constrained novel amino acids: β-isopropyltyrosines. Tetrahedron Asymmetry 8, 3213-3221.
9. Wang, S., Tang, X. & Hruby, V.J. (2000) First stereoselective synthesis of an optically pure β-substituted histidine: (2S,3S)-β-methylhistidine. Tetrahedron Lett. 41, 1307-1310.
10. Han, G., Lewis, A. & Hruby, V.J. (2001) Synthesis of (2S,3S)-β-methyltryptophan. Tetrahedron Lett. 41, 4601-4603.
11. Wang, W., Xiong, C., Zhang, J. & Hruby, V.J. (2002) Practical, asymmetric synthesis of aromatic-substituted bulky and hydrophobic tryptophan and phenylalanine derivatives. Tetrahedron 58, 3101-3110.
12. Cai, C., Yamada, T., Tiwari, R. & Hruby, V.J. (2004) Application of (S)-and (R)-methyl pyroglutamates as inexpensive, yet highly efficient chiral auxiliaries in the asymmetric Michael addition reactions. Tetrahedron Lett. 45, 6855-6858.
13. Lin, J., Liao, S. & Hruby, V.J. (2005) Syntheses of optically pure, conformationally constrained, and highly hydrophobic unusual amino acids: 2-amino-3, 3-diarylpropionic acids. J. Pept. Res. 65, 105-112.
14. Davies, S.G. & Sanganee, H.J. (1995) 4-Substituted-5,5-dimethyl oxazolidin-2-ones as effective chiral auxiliaries for enolate alkylations and Michael additions. Tetrahedron Asymmetry 6, 671-674.
15. Bull, S.G., Davies, S.G., Jones, S., Polywka, M.E.C., Prasad, R.S. & Sanganee, H.J. (1998) A practical procedure for the Multigram synthesis of the SuperQuat chiral auxiliaries. Synlett 5, 519-521.
16. Davies, S.G., Sanganee, H.J. & Szolcsanyi, P. (1999) The 'SuperQuat' (R)-4-phenyl-5,5-dimethyl oxazolidin-2-one as an effective chiral auxiliary for conjugate additions: asymmetric synthesis of (-)-aplysillamide B. Tetrahedron 55, 3337-3354.
17. Bull, S.D., Davies, S.G., Nicholson, R.L., Sanganee, H.J. & Smith, A.D. (2000) SuperQuat, (S)-4-benzyl-5,5-dimethyl-oxazolidin-2-one for the asymmetric synthesis of α-substituted-aldehydes. Tetrahedron Asymmetry 11, 3475-3479.