Exo,exo-2,3-diaminoborneol-derived imidazolidinone as chiral auxiliary for asymmetric alkylations

Tetrahedron Letters

Volumn 37, Issue 26, 1996, Pages 4565-4568

  Palomo, Claudio ^a   Oiarbide, Mikel ^a   González, Alberto ^b   García, Jesús M ^b   Berrée, Fabienne ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b PUBLIC UNIVERSITY OF NAVARRE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPHOR; IMIDAZOLE DERIVATIVE; OXAZOLIDINONE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; ORGANIC CHEMISTRY; STEREOCHEMISTRY; SYNTHESIS;

DRYOBALANOPS;

EID: 0030600159     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00847-7     Document Type: Article

References (23)

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9. 3. For a review on tert-leucine, see: Bonmarius, A.S.; Schwarm, M.S.; Stingl, K.; Kottenhanhn, M.; Huthmacher, K.; Drauz, K. Tetrahedron Asymmetry 1995, 6, 2851. For a review on camphor-derived chiral auxiliaries, see: Oppolzer, W. Tetrahedron 1987, 43, 1969.
10. 3. For a review on tert-leucine, see: Bonmarius, A.S.; Schwarm, M.S.; Stingl, K.; Kottenhanhn, M.; Huthmacher, K.; Drauz, K. Tetrahedron Asymmetry 1995, 6, 2851. For a review on camphor-derived chiral auxiliaries, see: Oppolzer, W. Tetrahedron 1987, 43, 1969.
11. 4. For asymmetric enolate alkylations on N-acyl imidazolidin-2-ones, see, for example: (a) Cardillo, G.; Orena, M.; Romero, M.; Sandri, S. Tetrahedron 1989, 45, 1501.
12. (b) Cardillo, G.; D'Amico, A.; Orena, M.; Sandri, S. J. Org. Chem. 1988, 53, 2354.
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15. (e) Davies, S.G.; Evans, G.B.; Mortlock, A.A. Tetrahedron Asymmetry 1994, 5, 585.
16. For an extensive list of references concerning other chiral auxiliaries, see: (f) Suder, A.; Hintermann, T.; Seebach, D. Helv. Chim. Acta 1995, 78, 1185.
17. 5. (a) Saigo, K.; Yamamoto, M.; Morimura, K.; Nohira, H. Chem. Lett. 1979, 545.
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19. 13C NMR 148.2, 140.4, 129.2, 128.5, 128.1, 127.0, 115.7, 112.4, 69.4, 60.2, 55.8, 48.9, 48.8, 47.0, 36.7, 25.6, 21.8, 21.0, 12.1
20. 2O: C, 75.52%; H, 8.20%; N, 10.36%. Found: C, 75.47%; H, 8.67%; N, 10.20%.
21. 8. Evans, D.A.; Ennis, M.D.; Mathre, D.J. J. Am. Chem. Soc. 1982, 104, 1737.
22. 9. Less reactive alkyl bromides such as n-propyl bromide and isobutyl iodide afforded very low yields of the expected products. For a solution to this problem which is general for imide enolates, see: Evans, D.A.; Dow, R.L.; Shih, L.; Takacs, J.M.; Zahler, R. J. Am. Chem. Soc. 1990, 112, 5290.
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