Stereoselective synthesis of anti-β-amino-α-hydroxy acid derivatives using nucleophilic epoxidation of 1-arylthio-1-nitroalkenes

Tetrahedron Letters

Volumn 37, Issue 13, 1996, Pages 2311-2314

  Ambroise, Lydia ^a   Jackson, Richard F W ^a  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029945593     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00252-3     Document Type: Article

References (22)

1. For recent synthetic approaches, see: Bunnage, M.E.; Chernega, A.N.; Davies, S.G.; Goodwin, C.J. J. Chem. Soc., Perkin Trans. 1 1994, 2373. Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. J. Chem. Soc., Perkin Trans. 1 1994, 2385.
2. For recent synthetic approaches, see: Bunnage, M.E.; Chernega, A.N.; Davies, S.G.; Goodwin, C.J. J. Chem. Soc., Perkin Trans. 1 1994, 2373. Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. J. Chem. Soc., Perkin Trans. 1 1994, 2385.
3. Dondoni, A.; Perrone, D.; Semola, T. Synthesis 1995, 181, and references therein.
4. For an overview, see: Nicolaou, K.C.; Dai, W.M.; Guy, R.K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15.
5. For previous synthetic work on allophenylnorstatine, see: Bunnage, M.E.; Davies, S.G.; Goodwin, C.J.; Ichihara, O. Tetrahedron, 1994, 50, 3975, and references therein.
6. Jackson, R.F.W.; Palmer, N.J.; Wythes, M.J.; Clegg, W.; Elsegood, M.R.J. J.Org. Chem. 1995, 60, 6431.
7. Jackson, R.F.W.; Palmer, N.J.; Wythes, M.J. Tetrahedron Lett. 1994, 35, 7433.
8. Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149.
9. Miyashita, M.; Kumazawa T.; Yoshikoshi, A. J. Org. Chem. 1980, 45, 2945; Barrett, A.G.M.; Graboski, G.G.; Russell, M.A. J. Org. Chem. 1986, 51, 1012; Barrett, A.G.M. Chem. Soc. Rev. 1991, 20, 95.
10. Miyashita, M.; Kumazawa T.; Yoshikoshi, A. J. Org. Chem. 1980, 45, 2945; Barrett, A.G.M.; Graboski, G.G.; Russell, M.A. J. Org. Chem. 1986, 51, 1012; Barrett, A.G.M. Chem. Soc. Rev. 1991, 20, 95.
11. Miyashita, M.; Kumazawa T.; Yoshikoshi, A. J. Org. Chem. 1980, 45, 2945; Barrett, A.G.M.; Graboski, G.G.; Russell, M.A. J. Org. Chem. 1986, 51, 1012; Barrett, A.G.M. Chem. Soc. Rev. 1991, 20, 95.
12. Determined in the case of 8b by chiral phase HPLC analysis using a sample prepared from D-phenylalanine for comparison.
13. Dondoni (reference 2) has reported the condensation of the aldehyde 4c (ee = 84%) with 2-(trimethylsilyl)-thiazole, which proceeds with no loss of optical purity, so we believe that it is the conditions of our condensation reaction which result in racemisation.
14. For a recent discussion of the coupling constants observed in related oxazolidinones, see: Kise, N.; Inakoshi, N.; Matsumura, Y. Tetrahedron Lett. 1995, 36, 909.
15. 3) to the corresponding tert-butyl ester 12b for comparison with a known compound, see reference 4 above. A small amount of the corresponding trans-oxazolidinone 12a, which could not be separated by chromatography, was always present, so direct comparison of specific rotation with the literature value could not be made. equation presented
16. Clegg, W. and Elsegood, M.R.J., unpublished work. The details of these crystal structure determinations will be published separately.
17. It is interesting to note that an isomerisation in the opposite sense has been observed in the preparation of Taxotere® using an isopropylidene protected derivative of anti-phenylisoserine: Denis, J.-N.; Kanazawa, A.M.; Greene, A.E. Tetrahedron Lett. 1994, 35, 105. See also reference 10 above.
18. Both diastereoisomers of closely related esters, in contrast to the thioesters which we have prepared, are reported in reference 11 above to be stable to silica gel chromatography. It therefore appears that the thioester group is responsible for the observed isomerisation to the cis-oxazolidinones.
19. Hoffmann, R.W. Chem. Rev. 1989, 89, 1841.
20. Chérest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199; Chérest, M.; Felkin, H. Tetrahedron Lett. 1968, 2205; Anh, N.T. Top. Curr. Chem. 1980, 88, 145.
21. Chérest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199; Chérest, M.; Felkin, H. Tetrahedron Lett. 1968, 2205; Anh, N.T. Top. Curr. Chem. 1980, 88, 145.
22. Chérest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199; Chérest, M.; Felkin, H. Tetrahedron Lett. 1968, 2205; Anh, N.T. Top. Curr. Chem. 1980, 88, 145.