The chromium-reformatsky reaction: Anti-selective evans-type aldol reactions with excellent inverse induction at ambient temperature

Tetrahedron Letters

Volumn 38, Issue 25, 1997, Pages 4387-4388

  Gabriel, Tobias ^a   Wessjohann, Ludger ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CHROMIUM CHLORIDE; HALIDE; OXAZOLIDINONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TEMPERATURE;

EID: 0030902795     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00952-0     Document Type: Article

References (18)

1. Ito, Y.; Terashima, S. Tetrahedron 1991, 47, 2821-2834; Braun, M.; Vonderhagen, A.; Waldmüller, D. Liebigs Ann. Chem. 1995, 1447-1450; Brandänge, S.; Josefson, S.; Mörch, L.; Vallén, S. Acta Chem. Scand., Ser. B 1981, 35, 273-277; Pini, D.; Mastantuono, A.; Salvadori, P. Tetrahedron: Asymmetry 1994, 5, 1875-1876; and refs. cited.
2. Ito, Y.; Terashima, S. Tetrahedron 1991, 47, 2821-2834; Braun, M.; Vonderhagen, A.; Waldmüller, D. Liebigs Ann. Chem. 1995, 1447-1450; Brandänge, S.; Josefson, S.; Mörch, L.; Vallén, S. Acta Chem. Scand., Ser. B 1981, 35, 273-277; Pini, D.; Mastantuono, A.; Salvadori, P. Tetrahedron: Asymmetry 1994, 5, 1875-1876; and refs. cited.
3. Ito, Y.; Terashima, S. Tetrahedron 1991, 47, 2821-2834; Braun, M.; Vonderhagen, A.; Waldmüller, D. Liebigs Ann. Chem. 1995, 1447-1450; Brandänge, S.; Josefson, S.; Mörch, L.; Vallén, S. Acta Chem. Scand., Ser. B 1981, 35, 273-277; Pini, D.; Mastantuono, A.; Salvadori, P. Tetrahedron: Asymmetry 1994, 5, 1875-1876; and refs. cited.
4. Ito, Y.; Terashima, S. Tetrahedron 1991, 47, 2821-2834; Braun, M.; Vonderhagen, A.; Waldmüller, D. Liebigs Ann. Chem. 1995, 1447-1450; Brandänge, S.; Josefson, S.; Mörch, L.; Vallén, S. Acta Chem. Scand., Ser. B 1981, 35, 273-277; Pini, D.; Mastantuono, A.; Salvadori, P. Tetrahedron: Asymmetry 1994, 5, 1875-1876; and refs. cited.
5. Fürstner, A. Synthesis 1989, 571-590; Rathke, M. W.; Weipert, P. Zinc Enolates: The Reformatsky and Blaise Reactions. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: Oxford, 1991; Vol. 2; pp. 277.
6. Fürstner, A. Synthesis 1989, 571-590; Rathke, M. W.; Weipert, P. Zinc Enolates: The Reformatsky and Blaise Reactions. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: Oxford, 1991; Vol. 2; pp. 277.
7. Braun, M. Formation of C-C Bonds by Addition of Enolates to Carbonyl Groups: Chiral Amide and Imide Enolates. In (Houben-Weyl) Stereoselective Synthesis; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. Eds.; Thieme Verlag: Stuttgart, 1995; Vol. E21b; 1644-1660; Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
8. Braun, M. Formation of C-C Bonds by Addition of Enolates to Carbonyl Groups: Chiral Amide and Imide Enolates. In (Houben-Weyl) Stereoselective Synthesis; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. Eds.; Thieme Verlag: Stuttgart, 1995; Vol. E21b; 1644-1660; Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
9. Wessjohann, L.; Wild, H. Synlett 1997, in press; Wessjohann, L.; Wild, H. Synthesis 1997, in press.
10. Wessjohann, L.; Wild, H. Synlett 1997, in press; Wessjohann, L.; Wild, H. Synthesis 1997, in press.
11. Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 38, 1363-1366.
12. Wessjohann, L. A.; Gabriel, T. J. Org. Chem. 1997, 62, in press.
13. Braun, M. Angew. Chem. 1987, 99, 24-37; Angew. Chem. Int. Ed. Engl. 1987, 26, 24. For an excellent chiral acetyl derivative of basic nature see: Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397-406 . For Mukaiyama type reactions of acidic nature, e. g. with Oppolzer-and Helmchen-auxiliaries, see lit. covered in ref. 3 (Braun), pp. 1636.
14. Braun, M. Angew. Chem. 1987, 99, 24-37; Angew. Chem. Int. Ed. Engl. 1987, 26, 24. For an excellent chiral acetyl derivative of basic nature see: Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397-406 . For Mukaiyama type reactions of acidic nature, e. g. with Oppolzer-and Helmchen-auxiliaries, see lit. covered in ref. 3 (Braun), pp. 1636.
15. Braun, M. Angew. Chem. 1987, 99, 24-37; Angew. Chem. Int. Ed. Engl. 1987, 26, 24. For an excellent chiral acetyl derivative of basic nature see: Devant, R.; Mahler, U.; Braun, M. Chem. Ber. 1988, 121, 397-406 . For Mukaiyama type reactions of acidic nature, e. g. with Oppolzer-and Helmchen-auxiliaries, see lit. covered in ref. 3 (Braun), pp. 1636.
16. The provisional assignments reported in our previous communication (ref. 5) for compounds 10-16 were based on analogy to titanium enolates and the "non-Evans" induction found with propionyl derivatives, and some confusion in the literature (for clarification cf. ref. 10). Most unfortunately the assignment of acid 11, the absolute configuration of which was supported by optical rotation, was obtained from a batch of (S)-oxazolidone (S)-9 mislabeled and accordingly shown as (R)-9. Thus (R)-9 must be replaced by (S)-9 in the text, and in scheme 3 of ref. 5 the configuration of the oxazolidone moiety must be inverted, whereas scheme 2 gives the correct stereochemistry with (R)-7b as Reformatsky substrate (based on the optical rotation of derivatives, NMR and the X-ray of a similar compound).
17. Walker, M. M.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747-5750.
18. Nerz-Stormes, M.; Thornton, E. R. J. Org. Chem. 1991, 56, 2489-2498.