(R)- and (S)-Enantioselective lithiation of (arene)tricarbonylchromium acetal complexes with chiral alkyllithiums

Chemical Communications

Volumn , Issue 20, 1996, Pages 2359-2360

  Siwek, Michael J ^a   Green, James R ^a  

^a UNIVERSITY OF WINDSOR   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002055047     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960002359     Document Type: Article

References (28)

1. A. Solladié-Cavallo, Adv. Met. Org. Chem., 1989, 1, 99; S. G. Davies, S. J. Coote and C. L. Goodfellow, Adv. Met. Org. Chem., 1991, 2, 1; M. Uemura, Adv. Met. Org. Chem., 1991, 2, 145; S. G. Davies and T. J. Donohue, Synlett, 1993, 323.
2. A. Solladié-Cavallo, Adv. Met. Org. Chem., 1989, 1, 99; S. G. Davies, S. J. Coote and C. L. Goodfellow, Adv. Met. Org. Chem., 1991, 2, 1; M. Uemura, Adv. Met. Org. Chem., 1991, 2, 145; S. G. Davies and T. J. Donohue, Synlett, 1993, 323.
3. A. Solladié-Cavallo, Adv. Met. Org. Chem., 1989, 1, 99; S. G. Davies, S. J. Coote and C. L. Goodfellow, Adv. Met. Org. Chem., 1991, 2, 1; M. Uemura, Adv. Met. Org. Chem., 1991, 2, 145; S. G. Davies and T. J. Donohue, Synlett, 1993, 323.
4. A. Solladié-Cavallo, Adv. Met. Org. Chem., 1989, 1, 99; S. G. Davies, S. J. Coote and C. L. Goodfellow, Adv. Met. Org. Chem., 1991, 2, 1; M. Uemura, Adv. Met. Org. Chem., 1991, 2, 145; S. G. Davies and T. J. Donohue, Synlett, 1993, 323.
5. Y. Kondo, J. R. Green and J. Ho, J. Org. Chem., 1993, 58, 6182 and references cited therein; J. Aubé, J. A. Heppert, M. L. Milligan, M. J. Smith and P. Zenk, J. Org. Chem., 1992, 57, 3563; S. G. Davies, T. Loveridge and J. M. Clough, J. Chem. Soc., Chem. Commun., 1995, 817; A. Alexakis and K. Tonis, Tetrahedron: Asymmetry, 1995, 6, 47; M. Uemura, A. Daimon and Y. Hayashi, J. Chem. Soc., Chem. Commun., 1995, 1943.
6. Y. Kondo, J. R. Green and J. Ho, J. Org. Chem., 1993, 58, 6182 and references cited therein; J. Aubé, J. A. Heppert, M. L. Milligan, M. J. Smith and P. Zenk, J. Org. Chem., 1992, 57, 3563; S. G. Davies, T. Loveridge and J. M. Clough, J. Chem. Soc., Chem. Commun., 1995, 817; A. Alexakis and K. Tonis, Tetrahedron: Asymmetry, 1995, 6, 47; M. Uemura, A. Daimon and Y. Hayashi, J. Chem. Soc., Chem. Commun., 1995, 1943.
7. Y. Kondo, J. R. Green and J. Ho, J. Org. Chem., 1993, 58, 6182 and references cited therein; J. Aubé, J. A. Heppert, M. L. Milligan, M. J. Smith and P. Zenk, J. Org. Chem., 1992, 57, 3563; S. G. Davies, T. Loveridge and J. M. Clough, J. Chem. Soc., Chem. Commun., 1995, 817; A. Alexakis and K. Tonis, Tetrahedron: Asymmetry, 1995, 6, 47; M. Uemura, A. Daimon and Y. Hayashi, J. Chem. Soc., Chem. Commun., 1995, 1943.
8. Y. Kondo, J. R. Green and J. Ho, J. Org. Chem., 1993, 58, 6182 and references cited therein; J. Aubé, J. A. Heppert, M. L. Milligan, M. J. Smith and P. Zenk, J. Org. Chem., 1992, 57, 3563; S. G. Davies, T. Loveridge and J. M. Clough, J. Chem. Soc., Chem. Commun., 1995, 817; A. Alexakis and K. Tonis, Tetrahedron: Asymmetry, 1995, 6, 47; M. Uemura, A. Daimon and Y. Hayashi, J. Chem. Soc., Chem. Commun., 1995, 1943.
9. Y. Kondo, J. R. Green and J. Ho, J. Org. Chem., 1993, 58, 6182 and references cited therein; J. Aubé, J. A. Heppert, M. L. Milligan, M. J. Smith and P. Zenk, J. Org. Chem., 1992, 57, 3563; S. G. Davies, T. Loveridge and J. M. Clough, J. Chem. Soc., Chem. Commun., 1995, 817; A. Alexakis and K. Tonis, Tetrahedron: Asymmetry, 1995, 6, 47; M. Uemura, A. Daimon and Y. Hayashi, J. Chem. Soc., Chem. Commun., 1995, 1943.
10. D. A. Price, N. S. Simpkins, A. M. MacLeod and A. P. Wall, J. Org. Chem., 1994, 59, 1961; E. P. Kündig, and A. Quattropani, Tetrahedron Lett., 1994, 35, 3497; D. A. Price, N. S. Simpkins, A. M. MacLeod and A. P. Watt, Tetrahedron Lett., 1994, 35, 6159; H.-G. Schmalz and K. Schellhaas, Tetrahedron Lett., 1995, 36, 5515.
11. D. A. Price, N. S. Simpkins, A. M. MacLeod and A. P. Wall, J. Org. Chem., 1994, 59, 1961; E. P. Kündig, and A. Quattropani, Tetrahedron Lett., 1994, 35, 3497; D. A. Price, N. S. Simpkins, A. M. MacLeod and A. P. Watt, Tetrahedron Lett., 1994, 35, 6159; H.-G. Schmalz and K. Schellhaas, Tetrahedron Lett., 1995, 36, 5515.
12. D. A. Price, N. S. Simpkins, A. M. MacLeod and A. P. Wall, J. Org. Chem., 1994, 59, 1961; E. P. Kündig, and A. Quattropani, Tetrahedron Lett., 1994, 35, 3497; D. A. Price, N. S. Simpkins, A. M. MacLeod and A. P. Watt, Tetrahedron Lett., 1994, 35, 6159; H.-G. Schmalz and K. Schellhaas, Tetrahedron Lett., 1995, 36, 5515.
13. D. A. Price, N. S. Simpkins, A. M. MacLeod and A. P. Wall, J. Org. Chem., 1994, 59, 1961; E. P. Kündig, and A. Quattropani, Tetrahedron Lett., 1994, 35, 3497; D. A. Price, N. S. Simpkins, A. M. MacLeod and A. P. Watt, Tetrahedron Lett., 1994, 35, 6159; H.-G. Schmalz and K. Schellhaas, Tetrahedron Lett., 1995, 36, 5515.
14. A. Alexakis, T. Kanger, P. Mangeney, F. Rose-Munch and E. Rose, Tetrahedron: Asymmetry, 1995, 6, 2135.
15. For the use of alkyllithiums with chiral diamines, see: M. Uemura, Y. Hayashi and Y. Hayashi, Tetrahedron: Asymmetry, 1994, 5, 1427.
16. Recent work has also demonstrated the effectiveness of chiral lithium amides at enantioselective benzylic lithiation of benzylic ether complexes: R. A. Ewin and N. S. Simpkins, Synlett, 1996, 317; E. L. M. Cowton, S. E. Gibson, M. J. Schneider and M. H. Smith, Chem. Commun., 1996, 839.
17. Recent work has also demonstrated the effectiveness of chiral lithium amides at enantioselective benzylic lithiation of benzylic ether complexes: R. A. Ewin and N. S. Simpkins, Synlett, 1996, 317; E. L. M. Cowton, S. E. Gibson, M. J. Schneider and M. H. Smith, Chem. Commun., 1996, 839.
18. V. Snieckus, Chem. Rev., 1940, 90, 879.
19. S. G. Davies and C. L. Goodfellow, J. Chem. Soc., Perkin Trans. 1, 1990, 393; J. A. Heppert, J. Aubé, M. E. Thomas-Miller, M. L. Milligan and F. Takusagawa, Organometallics, 1990, 9, 727; J. Blagg, S. G. Davies, C. L. Goodfellow and K. H. Sutton, J. Chem. Soc., Perkins Trans. 1, 1987, 1805.
20. S. G. Davies and C. L. Goodfellow, J. Chem. Soc., Perkin Trans. 1, 1990, 393; J. A. Heppert, J. Aubé, M. E. Thomas-Miller, M. L. Milligan and F. Takusagawa, Organometallics, 1990, 9, 727; J. Blagg, S. G. Davies, C. L. Goodfellow and K. H. Sutton, J. Chem. Soc., Perkins Trans. 1, 1987, 1805.
21. S. G. Davies and C. L. Goodfellow, J. Chem. Soc., Perkin Trans. 1, 1990, 393; J. A. Heppert, J. Aubé, M. E. Thomas-Miller, M. L. Milligan and F. Takusagawa, Organometallics, 1990, 9, 727; J. Blagg, S. G. Davies, C. L. Goodfellow and K. H. Sutton, J. Chem. Soc., Perkins Trans. 1, 1987, 1805.
22. W. H. Glaze and C. M. Selman, J. Org. Chem. 1968, 33, 1987; A. Maercker, R. Schuhmacher, W. Buchmeier and H. D. Lutz, Chem. Ber., 1991, 124, 2489.
23. W. H. Glaze and C. M. Selman, J. Org. Chem. 1968, 33, 1987; A. Maercker, R. Schuhmacher, W. Buchmeier and H. D. Lutz, Chem. Ber., 1991, 124, 2489.
24. P. K. Freeman and L. L. Hutchinson, J. Org. Chem., 1980, 45, 1924; P. K. Freeman and L. L. Hutchinson, J. Org. Chem., 1983, 48, 4705.
25. P. K. Freeman and L. L. Hutchinson, J. Org. Chem., 1980, 45, 1924; P. K. Freeman and L. L. Hutchinson, J. Org. Chem., 1983, 48, 4705.
26. A. Solladié-Cavallo and J. Suffert, Magn. Reson. Chem., 1985, 23, 739.
27. J. K. Whitesell, Chem. Rev., 1992, 92, 953.
28. O. Ostwald, Org. Synth., 1987, 65, 203.