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Volumn 62, Issue 21, 1997, Pages 7364-7375

Preparation and Use of Aziridino Alcohols as Promoters for the Enantioselective Addition of Dialkylzinc Reagents to N-(Diphenylphosphinoyl) Imines

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EID: 0001010190     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970918h     Document Type: Article
Times cited : (129)

References (62)
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    • (1983) Asymmetric Synthesis , vol.2 A
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    • For a review, see: (a) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. (b) Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895.
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    • See, for example: (a) Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204. (b) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. (c) Tanner, D.; Somfai, P. Tetrahedron Lett. 1987, 28, 1211. (d) Tanner, D.; He, H. M. Tetrahedron 1992, 48, 6079.
    • (1977) Helv. Chim. Acta , vol.60 , pp. 204
    • Oppolzer, W.1    Flaskamp, E.2
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    • See, for example: (a) Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204. (b) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. (c) Tanner, D.; Somfai, P. Tetrahedron Lett. 1987, 28, 1211. (d) Tanner, D.; He, H. M. Tetrahedron 1992, 48, 6079.
    • (1987) J. Chem. Soc., Chem. Commun. , pp. 153
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    • See, for example: (a) Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204. (b) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. (c) Tanner, D.; Somfai, P. Tetrahedron Lett. 1987, 28, 1211. (d) Tanner, D.; He, H. M. Tetrahedron 1992, 48, 6079.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 1211
    • Tanner, D.1    Somfai, P.2
  • 21
    • 0026748273 scopus 로고
    • See, for example: (a) Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204. (b) Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153. (c) Tanner, D.; Somfai, P. Tetrahedron Lett. 1987, 28, 1211. (d) Tanner, D.; He, H. M. Tetrahedron 1992, 48, 6079.
    • (1992) Tetrahedron , vol.48 , pp. 6079
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    • note
    • A sample of ligand 3a was recovered from two successive stoichiometric reactions and it was used to set up a catalytic (0.50 equiv of 3a) addition reaction to the imine 1a. The expected product was isolated in 79% yield and 81% ee, a value that is only slightly lower than the one obtained in the same catalytic reaction but using fresh ligand (Table 2, entry 1).
  • 56
    • 1542424175 scopus 로고    scopus 로고
    • We are grateful to Dr. Adolf Gogoll for helping to set up the experiment and to interpret the data
    • We are grateful to Dr. Adolf Gogoll for helping to set up the experiment and to interpret the data.
  • 57
    • 1542528888 scopus 로고    scopus 로고
    • The product was very hygroscopic
    • The product was very hygroscopic.


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