Allyl silane additions to highly electrophilic 5, 6-Dihydro-2H-1, 4-oxazinones

Letters in Organic Chemistry

Volumn 6, Issue 3, 2009, Pages 224-228

  Shafer, Cynthia M ^a,d   Pigzaa, Julie ^b   Molinski, Tadeusz F ^b,c,d  

^a NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

^b Department of Chemistry and Biochemistry ^*  (United States)

^c UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^d UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Amino acid; Imine; Morpholinone; Oxazinone

Indexed keywords

EID: 69249219210     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017809787893046     Document Type: Article

References (32)

1. Shafer, C.M.; Molinski, T.F. J. Org. Chem., 1996, 61, 2044-2050.
2. Shafer, C.M. PhD Thesis, 1998, University of California, Davis, 1998.
3. Harwood, L.M.; Tyler, S.N.G.; Anslow, A.S.; MacGilp, I.D.; Drew, M.G.B. Tetrahedron Asymmetry, 1997, 8, 4007.
4. 3-Bromo-5, 6-diphenyl-5, 6-dihydrooxazinones have been used as chiral electrophilic glycine equivalents (see also preceding reference) in additions of organozincs, cuprates, silylketene acetals, enolsilanes, allylsilane and other nucleophiles.Williams, R.M.; Sinclair, P.J.; Zhai, D.; Chen, D. J. Am. Chem. Soc., 1988, 110, 1547.
5. Sinclair, P.J.; Zhai, D.; Reibenspies, J.; Williams, R.M. J. Am. Chem. Soc., 1986, 108, 1103. In the latter report, the intermediate of the reaction was presumed to be an oxazinone (c.f. 1) but was never isolated.
6. Andersen, R.J.; Coleman, J.E.; Piers, E.P.; Wallace, D.J. Tetrahedron Lett., 1997, 38, 317-320.
7. Hamada, T.; Sugawara, T.; Matsunaga, S.; Fusetani, N. Tetrahedron Lett., 1994, 35, 719.
8. Hamada, T.; Matsunaga, S.; Yano, G.; Fusetani, N. J. Am. Chem. Soc., 2005, 127, 110.
9. Chu, K.S.; Negrete, G.R.; Konopelski, J.P.; Lakner, F.J.; Woo, N.-T.; Olmstead, M.M. J. Am. Chem. Soc., 1992, 114, 1800.
10. Chu, K.S.; Negrete, G.R.; Konopelski, J.P. J. Org. Chem., 1991, 56, 5196.
11. Schöellkopf, U.; Neubauer, H. J. Synthesis, 1982, 10, 861.
12. Dellaria, J.F.; Santarsiero, B.D. J. Org. Chem., 1989, 54, 3916.
13. Groth, U.; Halfbrodt, W.; Schöellkopf, U. Liebigs Ann. Chem., 1992, 4, 351.
14. O'Donnell, M.J. Aldrichimica Acta, 2001, 34, 3.
15. O'Donnell, M.J.; Boniece, J.M.; Earp, S.E. Tetrahedron Lett., 1978, 19, 2641.
16. Lygo, B.; Wainwright, P.G. Tetrahedron Lett., 1997, 38, 8595.
17. Corey, E.J.; Xu, F.; Noe, M.C. J. Am. Chem. Soc., 1997, 119, 12414.
18. Corey, E.J.; Noe, M.C.; Xu, F. Tetrahedron Lett., 1998, 39, 5347.
19. Williams, R.M. Synthesis of Optically Active ?̀?-Amino Acids, Pergamon: Oxford, 1989.
20. Currie, G.S.; Drew, M.G.B.; Harwood, L.M.; Hughes, D.J.; Luke, R.W.A.; Vickers, R.J. J. Chem. Soc. Perkin Trans. I, 2000, 2982.
21. Liu, C.; Masuno, M.N.; MacMillan, J.B.; Molinski, T.F. Angew. Chem. Int. Ed. Engl, 2004, 43, 5951.
22. 2 shows only pseudo-equatorial C5 phenyl groups but 'heterogeneity' of oxazinone ring conformations [2].
23. It is more difficult to predict the effect of the more bulky allyl silanes ii and iii upon facial selectivity towards 1a. The erosion in diastereoselectivity seen in entries 3 and 4 may be reflect perturbation of this simple internally coordinated transition state model by the more hindered silane or an alternate mechanism involving an 'open transition' state.
24. A recent report by Fukuyama and coworkers highlight the utility of 1d (Scheme (1)), a 6, 6-gem-dimethylsubstituted homolog of 1b that was prepared from (S)-phenylglycine methyl ester in six steps. Tohma, S.; Rikimaru, K.; Endo, A.; Shimamoto, K.; Kan, T.; Fukuyama, T. Synthesis 2004, 909. Oxazinone 1d undergoes addition with i in the presence of TFA to give the corresponding 3-allyl-2- morpholinone single diastereomer in 88% yield.
25. Meyers, A.I.; Knaus, G.; Kamata, K.; Ford, M.E. J. Am. Chem. Soc., 1976, 98, 567.
26. Allen, Jr., Paul; Ginos, J. J. Org. Chem., 1963, 28, 2759.
27. Gorunova, O.N.; Keuseman, K.J.; Goebel, B.M.; Kataeva, N.A.; Churakov, A.V.; Kuz'mina, L.G.; Dunina, V.V.; Smoliakova, I.P. J. Organomet. Chem., 2004, 689, 2382.
28. Gossage, R.A.; Sadowy, A.L. Lett. Org. Chem., 2005, 2, 25.
29. Sakakura, A.; Kondo, R.; Ishihara, K. Org. Lett., 2005, 7, 1971.
30. Sakakura, A.; Kondo, R.; Umemura, S.; Ishihara, K. Tetrahedron, 2009, in press.
31. ent-15 (L-neopentylglycine) can be prepared by asymmetric twoenzyme- coupled catalyzed reductive amination on an industrial scale (~30 kg, Krix, G.; Bommarius, A.S.; Drauz, K.; Kottenhahn, M.; Schwarm, M.; Kula, M.-R. J. Biotech., 1997, 53, 29), however, no convenient synthesis of D-15 has been reported.
32. Ager, D.; Cooper, N.; Cox, G.G.; Garro-Hélion, F.; Harwood, L.M. Tetrahedron Asymmetry, 1996, 7, 2563.