Asymmetric induction in radical reactions: Enantioselective syntheses of (S)-2-deuterioglycine and (R)-2-deuterioglycine

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 5, 1991, Pages 332-333

  Hamon, David P G ^a   Razzino, Pasquale ^a   Massy Westropp, Ralph A ^a  

^a UNIVERSITY OF ADELAIDE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

DEUTERIUM; GLYCINE;

ARTICLE; CHEMICAL STRUCTURE; ISOTOPE LABELING;

EID: 0025978214     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39910000332     Document Type: Article

References (22)

1. B. Giese, Angew. Chem., Int. Ed. Engl., 1989, 28, 969
2. K. Ramalingam, P. Nanjappan, D.M. Kalvin and R.W. Woodard, Tetrahedron, 1988, 44, 5597, and references therein.
3. Y. Guindon, C. Yoakim, R. Lemieux, L. Boisvert, D. Delorme and J.-F. Lavallee, Tetrahedron Lett., 1990, 31, 2845
4. E.J. Corey and H.E. Ensley, J. Am. Chem. Soc., 1975, 97, 6908
5. O. Ort, Org. Synth, 1987, 65, 203
6. P. Ermert, J. Meyer, C. Stucki, J. Schneebeli and J.-P. Obrecht, Tetrahedron Lett., 1988, 29, 1265
7. P.J. Sinclair, D. Zhai, J. Reibenspies and R.W. Williams, J. Am. Chem. Soc., 1986, 108, 1103
8. R.M. Williams, P.J. Sinclair, D. Zhai and D. Chen, J. Am. Chem. Soc., 1988, 110, 1547
9. J. Zimmermann and D. Seebach, Helv. Chim. Acta, 1987, 70, 1104
10. W.L.F. Armarego, B.A. Milloy and W. Penderaast, J. Chem. Soc., Perkin Trans. 1, 1976, 2229
11. H.G. Viehe, R. Merenyi, L. Stella and Z. Janousek, Angew. Chem., Int. Ed. Engl., 1979, 18, 917
12. J.K. Whitesell, A. Bhattacharya and K. Henke, J. Chem. Soc., Chem. Commun., 1982, 988, The configuration with respect to the carbonyl groups is maintained, it is believed, by coordination with magnesium:
13. J.K. Whitesell, Acc. Chem. Res., 1985, 18, 280
14. V. Slet, H. Salandi, T. Lumiste and I. Arro, Eesti NSV Tead-Akad. Toim., Funs., Mat., 1976, 25, 46, Chemical Abstracts reports are confusing on this point:
15. V. Slet, H. Salandi, T. Lumiste and I. Arro, Chem. Abstr., 1976, 85, 160, 486
16. V. Slet, Tezisy Dokl.-Resp. Konf. Molodykh Uch.-Khim. 2nd, 1977, 2, 53
17. V. Slet, Chem. Abstr., 1980, 93, 132
18. C.J. Easton, I.M. Scharfbillig and E.W. Tan, Tetrahedron Lett., 1988, 29, 1565
19. J.E. Baldwin, R.M. Adlington, C. Lowe, I.A. O'Neil, G.L. Sanders, C.J. Schofield and J.B. Sweeney, J. Chem. Soc., Chem. Commun., 1988, 1030
20. D.P. Curran, W. Shen, J. Zhang and T.A. Heffner, J. Am. Chem. Soc., 1990, 112, 6738
21. N.A. Porter, E. Swann, J. Nally and A.T. McPhail, J. Am. Chem. Soc., 1990, 112, 6740
22. B. Biese, M. Zennder, M. Roth and H.-G. Zeitz, J. Am. Chem. Soc., 1990, 112, 6741