Auxiliary-controlled diastereoselection by N-(1-phenylethyl) in Grignard additions to 2-O-benzylglyceraldehyde imines

Chemical Communications

Volumn , Issue 3, 1996, Pages 329-330

  Veith, Ulrich ^a   Leurs, Stefan ^a   Jäger, Volker ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

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EID: 1842584396     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (36)

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7. Cf. use of iminium salts: S. Kano, Y. Yuasa, T. Yokomatsu and S. Shibuya, J. Org. Chem., 1988, 53, 3865; J.-i. Yamada, H. Satô and Y. Yamamoto, Tetrahedron Lett., 1989, 30, 5611; W.-J. Koot, R. van Ginkel, M. Kranenburg, H. Hiemstra, S. Louwrier, M. J. Moolenaar and W. N. Speckamp, Tetrahedron Lett., 1991, 32, 401; M. Nagai, J. J. Gaudino and C. S. Wilcox, Synthesis, 1992, 163.
8. Cf. use of iminium salts: S. Kano, Y. Yuasa, T. Yokomatsu and S. Shibuya, J. Org. Chem., 1988, 53, 3865; J.-i. Yamada, H. Satô and Y. Yamamoto, Tetrahedron Lett., 1989, 30, 5611; W.-J. Koot, R. van Ginkel, M. Kranenburg, H. Hiemstra, S. Louwrier, M. J. Moolenaar and W. N. Speckamp, Tetrahedron Lett., 1991, 32, 401; M. Nagai, J. J. Gaudino and C. S. Wilcox, Synthesis, 1992, 163.
9. Cf. use of iminium salts: S. Kano, Y. Yuasa, T. Yokomatsu and S. Shibuya, J. Org. Chem., 1988, 53, 3865; J.-i. Yamada, H. Satô and Y. Yamamoto, Tetrahedron Lett., 1989, 30, 5611; W.-J. Koot, R. van Ginkel, M. Kranenburg, H. Hiemstra, S. Louwrier, M. J. Moolenaar and W. N. Speckamp, Tetrahedron Lett., 1991, 32, 401; M. Nagai, J. J. Gaudino and C. S. Wilcox, Synthesis, 1992, 163.
10. Addition of RM to optically active, enolizable imines, see ref. 3, 4, 7. For recent papers see, for example: T. Fujisawa, M. Nagai, Y. Koike, M. Koike and M. Shimizu, J. Org. Chem., 1994, 59, 5865; L. Cippola, L. Lay, F. Nicotra, C. Pangrazio and L. Panza, Tetrahedron, 1995, 51, 4679.
11. Addition of RM to optically active, enolizable imines, see ref. 3, 4, 7. For recent papers see, for example: T. Fujisawa, M. Nagai, Y. Koike, M. Koike and M. Shimizu, J. Org. Chem., 1994, 59, 5865; L. Cippola, L. Lay, F. Nicotra, C. Pangrazio and L. Panza, Tetrahedron, 1995, 51, 4679.
12. (a) Y. Yamamoto, T. Komatsu and K. Maruyama. J. Chem. Soc., Chem. Commun., 1985, 814;
13. (b) Cf. methyl cuprate additions to (S)-(1-phenylethyl)imines of achiral aldehydes: C. Boga, D. Savoia and A. Umani-Ronchi, Tetrahedron: Asymmetry, 1990, 1, 291;
14. (c) additions to imines of chiral 2-amino alcohols: M. A. Scialdone and A. I. Meyers, Tetrahedron Lett., 1994, 41, 7533; use of β-alkoxy hydrazines: D. Enders, J. Schankat and M. Klatt, Synlett, 1994, 795;
15. (c) additions to imines of chiral 2-amino alcohols: M. A. Scialdone and A. I. Meyers, Tetrahedron Lett., 1994, 41, 7533; use of β-alkoxy hydrazines: D. Enders, J. Schankat and M. Klatt, Synlett, 1994, 795;
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17. (e) use of glyoxal-bis[(1-phenylethyl)imine]: K. Bambridge, M. I. Begley and N. S. Simpkins, Tetrahedron Lett., 1994, 35, 3391.
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