Alkylation of Tricarbonylchromium-Stabilized Benzylic Anions of 3-(Dipropylamino)chroman

Journal of Organic Chemistry

Volumn 63, Issue 16, 1998, Pages 5362-5367

  Brisander, Magnus ^a,b   Caldirola, Patrizia ^b   Johansson, Anette M ^b   Hacksell, Uli ^a,c  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b UPPSALA UNIVERSITY   (Sweden)

^c ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000697473     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980133r     Document Type: Article

References (34)

1. For reviews on tricarbonylchromium chemistry, see: (a) Solladié-Cavallo, A. Polyhedron 1985, 4, 901-927. (b) Solladié-Cavallo, A. In Advances in Metal-Organic Chemistry; JAI Press Inc.: Greenwich, CT, 1989; Vol. 1, pp 99-133. Davies, S. G.; Coote, S. J.; Goodfellow, C. L. In Advances in Metal-Organic Chemistry; JAI Press Ltd.: London, 1991; Vol. 2, pp 1-57. Uemura, M. In Advances in Metal-Organic Chemistry; JAI Press Ltd.: London, 1991; Vol. 2, pp 195-245. (e) Uemura, M. In Chains, Clusters, Inclusion Compounds, Paramagnetic Labels and Organic Rings; Zanello, P., Ed.; Elsevier Science Ltd.: New York, 1994; Vol. 5, pp 507-555.
2. For reviews on tricarbonylchromium chemistry, see: (a) Solladié-Cavallo, A. Polyhedron 1985, 4, 901-927. (b) Solladié-Cavallo, A. In Advances in Metal-Organic Chemistry; JAI Press Inc.: Greenwich, CT, 1989; Vol. 1, pp 99-133. Davies, S. G.; Coote, S. J.; Goodfellow, C. L. In Advances in Metal-Organic Chemistry; JAI Press Ltd.: London, 1991; Vol. 2, pp 1-57. Uemura, M. In Advances in Metal-Organic Chemistry; JAI Press Ltd.: London, 1991; Vol. 2, pp 195-245. (e) Uemura, M. In Chains, Clusters, Inclusion Compounds, Paramagnetic Labels and Organic Rings; Zanello, P., Ed.; Elsevier Science Ltd.: New York, 1994; Vol. 5, pp 507-555.
3. For reviews on tricarbonylchromium chemistry, see: (a) Solladié-Cavallo, A. Polyhedron 1985, 4, 901-927. (b) Solladié-Cavallo, A. In Advances in Metal-Organic Chemistry; JAI Press Inc.: Greenwich, CT, 1989; Vol. 1, pp 99-133. Davies, S. G.; Coote, S. J.; Goodfellow, C. L. In Advances in Metal-Organic Chemistry; JAI Press Ltd.: London, 1991; Vol. 2, pp 1-57. Uemura, M. In Advances in Metal-Organic Chemistry; JAI Press Ltd.: London, 1991; Vol. 2, pp 195-245. (e) Uemura, M. In Chains, Clusters, Inclusion Compounds, Paramagnetic Labels and Organic Rings; Zanello, P., Ed.; Elsevier Science Ltd.: New York, 1994; Vol. 5, pp 507-555.
4. For reviews on tricarbonylchromium chemistry, see: (a) Solladié-Cavallo, A. Polyhedron 1985, 4, 901-927. (b) Solladié-Cavallo, A. In Advances in Metal-Organic Chemistry; JAI Press Inc.: Greenwich, CT, 1989; Vol. 1, pp 99-133. Davies, S. G.; Coote, S. J.; Goodfellow, C. L. In Advances in Metal-Organic Chemistry; JAI Press Ltd.: London, 1991; Vol. 2, pp 1-57. Uemura, M. In Advances in Metal-Organic Chemistry; JAI Press Ltd.: London, 1991; Vol. 2, pp 195-245. (e) Uemura, M. In Chains, Clusters, Inclusion Compounds, Paramagnetic Labels and Organic Rings; Zanello, P., Ed.; Elsevier Science Ltd.: New York, 1994; Vol. 5, pp 507-555.
5. For reviews on tricarbonylchromium chemistry, see: (a) Solladié-Cavallo, A. Polyhedron 1985, 4, 901-927. (b) Solladié-Cavallo, A. In Advances in Metal-Organic Chemistry; JAI Press Inc.: Greenwich, CT, 1989; Vol. 1, pp 99-133. Davies, S. G.; Coote, S. J.; Goodfellow, C. L. In Advances in Metal-Organic Chemistry; JAI Press Ltd.: London, 1991; Vol. 2, pp 1-57. Uemura, M. In Advances in Metal-Organic Chemistry; JAI Press Ltd.: London, 1991; Vol. 2, pp 195-245. (e) Uemura, M. In Chains, Clusters, Inclusion Compounds, Paramagnetic Labels and Organic Rings; Zanello, P., Ed.; Elsevier Science Ltd.: New York, 1994; Vol. 5, pp 507-555.
6. For articles dealing with benzylic alkylation of tricarbonylchromium complexes, see: (a) Simonneaux, G.; Jaouen, G. Tetrahedron 1979, 35, 2249-2254. (b) Arzeno, H. B.; Barton, D. H. R.; Davies, S. G.; Lusinchi, X.; Meunier, B.; Pascard, C. Nouv. J. Chim. 1980, 4, 369-375. Jaouen, G.; Top, S.; Laconi, A.; Couturier, D.; Brocard, J. J. Am. Chem. Soc. 1984, 706, 2207-2208. Top, S.; Vessieres, A.; Abjean, J.-P.; Jaouen, G. J. Chem. Soc., Chem. Commun. 1984, 428-429. (e) Blagg, J.; Davies, S. G. J. Chem. Soc., Chem. Commun. 1985, 653-654. (f) Jaouen, G. Pure Appl. Chem. 1986, 58, 597-616. (g) Mathews, N.; Sainsbury, M. J. Chem. Res., Synop. 1988, 82-83. (h) Davies, S. G.; Goodfellow, C. L. J. Organomet. Chem. 1989, 370, C5-C8. Coote, S. J.; Davies, S. G.; Goodfellow, C. L.; Sutton, K. H.; Middlemiss, D.; Naylor, A. Tetrahedron: Asymmetry 1990, 1, 817-842. (j) Persson, M.; Hacksell, U. J. Chem. Soc., Perkin Trans, 1 1992, 131-135. (k) Davies, S. G.; Goodfellow, C. L.; Sutton, K. H. Tetrahedron: Asymmetry 1992, 3, 1303-1316. (l) Uemura, M.; Miyake, R.; Nakayama, K.; Shiro, M.; Hayashi, Y. J. Org. Chem. 1993, 58, 1238-1244.
7. For articles dealing with benzylic alkylation of tricarbonylchromium complexes, see: (a) Simonneaux, G.; Jaouen, G. Tetrahedron 1979, 35, 2249-2254. (b) Arzeno, H. B.; Barton, D. H. R.; Davies, S. G.; Lusinchi, X.; Meunier, B.; Pascard, C. Nouv. J. Chim. 1980, 4, 369-375. Jaouen, G.; Top, S.; Laconi, A.; Couturier, D.; Brocard, J. J. Am. Chem. Soc. 1984, 706, 2207-2208. Top, S.; Vessieres, A.; Abjean, J.-P.; Jaouen, G. J. Chem. Soc., Chem. Commun. 1984, 428-429. (e) Blagg, J.; Davies, S. G. J. Chem. Soc., Chem. Commun. 1985, 653-654. (f) Jaouen, G. Pure Appl. Chem. 1986, 58, 597-616. (g) Mathews, N.; Sainsbury, M. J. Chem. Res., Synop. 1988, 82-83. (h) Davies, S. G.; Goodfellow, C. L. J. Organomet. Chem. 1989, 370, C5-C8. Coote, S. J.; Davies, S. G.; Goodfellow, C. L.; Sutton, K. H.; Middlemiss, D.; Naylor, A. Tetrahedron: Asymmetry 1990, 1, 817-842. (j) Persson, M.; Hacksell, U. J. Chem. Soc., Perkin Trans, 1 1992, 131-135. (k) Davies, S. G.; Goodfellow, C. L.; Sutton, K. H. Tetrahedron: Asymmetry 1992, 3, 1303-1316. (l) Uemura, M.; Miyake, R.; Nakayama, K.; Shiro, M.; Hayashi, Y. J. Org. Chem. 1993, 58, 1238-1244.
8. For articles dealing with benzylic alkylation of tricarbonylchromium complexes, see: (a) Simonneaux, G.; Jaouen, G. Tetrahedron 1979, 35, 2249-2254. (b) Arzeno, H. B.; Barton, D. H. R.; Davies, S. G.; Lusinchi, X.; Meunier, B.; Pascard, C. Nouv. J. Chim. 1980, 4, 369-375. Jaouen, G.; Top, S.; Laconi, A.; Couturier, D.; Brocard, J. J. Am. Chem. Soc. 1984, 706, 2207-2208. Top, S.; Vessieres, A.; Abjean, J.-P.; Jaouen, G. J. Chem. Soc., Chem. Commun. 1984, 428-429. (e) Blagg, J.; Davies, S. G. J. Chem. Soc., Chem. Commun. 1985, 653-654. (f) Jaouen, G. Pure Appl. Chem. 1986, 58, 597-616. (g) Mathews, N.; Sainsbury, M. J. Chem. Res., Synop. 1988, 82-83. (h) Davies, S. G.; Goodfellow, C. L. J. Organomet. Chem. 1989, 370, C5-C8. Coote, S. J.; Davies, S. G.; Goodfellow, C. L.; Sutton, K. H.; Middlemiss, D.; Naylor, A. Tetrahedron: Asymmetry 1990, 1, 817-842. (j) Persson, M.; Hacksell, U. J. Chem. Soc., Perkin Trans, 1 1992, 131-135. (k) Davies, S. G.; Goodfellow, C. L.; Sutton, K. H. Tetrahedron: Asymmetry 1992, 3, 1303-1316. (l) Uemura, M.; Miyake, R.; Nakayama, K.; Shiro, M.; Hayashi, Y. J. Org. Chem. 1993, 58, 1238-1244.
9. For articles dealing with benzylic alkylation of tricarbonylchromium complexes, see: (a) Simonneaux, G.; Jaouen, G. Tetrahedron 1979, 35, 2249-2254. (b) Arzeno, H. B.; Barton, D. H. R.; Davies, S. G.; Lusinchi, X.; Meunier, B.; Pascard, C. Nouv. J. Chim. 1980, 4, 369-375. Jaouen, G.; Top, S.; Laconi, A.; Couturier, D.; Brocard, J. J. Am. Chem. Soc. 1984, 706, 2207-2208. Top, S.; Vessieres, A.; Abjean, J.-P.; Jaouen, G. J. Chem. Soc., Chem. Commun. 1984, 428-429. (e) Blagg, J.; Davies, S. G. J. Chem. Soc., Chem. Commun. 1985, 653-654. (f) Jaouen, G. Pure Appl. Chem. 1986, 58, 597-616. (g) Mathews, N.; Sainsbury, M. J. Chem. Res., Synop. 1988, 82-83. (h) Davies, S. G.; Goodfellow, C. L. J. Organomet. Chem. 1989, 370, C5-C8. Coote, S. J.; Davies, S. G.; Goodfellow, C. L.; Sutton, K. H.; Middlemiss, D.; Naylor, A. Tetrahedron: Asymmetry 1990, 1, 817-842. (j) Persson, M.; Hacksell, U. J. Chem. Soc., Perkin Trans, 1 1992, 131-135. (k) Davies, S. G.; Goodfellow, C. L.; Sutton, K. H. Tetrahedron: Asymmetry 1992, 3, 1303-1316. (l) Uemura, M.; Miyake, R.; Nakayama, K.; Shiro, M.; Hayashi, Y. J. Org. Chem. 1993, 58, 1238-1244.
10. For articles dealing with benzylic alkylation of tricarbonylchromium complexes, see: (a) Simonneaux, G.; Jaouen, G. Tetrahedron 1979, 35, 2249-2254. (b) Arzeno, H. B.; Barton, D. H. R.; Davies, S. G.; Lusinchi, X.; Meunier, B.; Pascard, C. Nouv. J. Chim. 1980, 4, 369-375. Jaouen, G.; Top, S.; Laconi, A.; Couturier, D.; Brocard, J. J. Am. Chem. Soc. 1984, 706, 2207-2208. Top, S.; Vessieres, A.; Abjean, J.-P.; Jaouen, G. J. Chem. Soc., Chem. Commun. 1984, 428-429. (e) Blagg, J.; Davies, S. G. J. Chem. Soc., Chem. Commun. 1985, 653-654. (f) Jaouen, G. Pure Appl. Chem. 1986, 58, 597-616. (g) Mathews, N.; Sainsbury, M. J. Chem. Res., Synop. 1988, 82-83. (h) Davies, S. G.; Goodfellow, C. L. J. Organomet. Chem. 1989, 370, C5-C8. Coote, S. J.; Davies, S. G.; Goodfellow, C. L.; Sutton, K. H.; Middlemiss, D.; Naylor, A. Tetrahedron: Asymmetry 1990, 1, 817-842. (j) Persson, M.; Hacksell, U. J. Chem. Soc., Perkin Trans, 1 1992, 131-135. (k) Davies, S. G.; Goodfellow, C. L.; Sutton, K. H. Tetrahedron: Asymmetry 1992, 3, 1303-1316. (l) Uemura, M.; Miyake, R.; Nakayama, K.; Shiro, M.; Hayashi, Y. J. Org. Chem. 1993, 58, 1238-1244.
11. For articles dealing with benzylic alkylation of tricarbonylchromium complexes, see: (a) Simonneaux, G.; Jaouen, G. Tetrahedron 1979, 35, 2249-2254. (b) Arzeno, H. B.; Barton, D. H. R.; Davies, S. G.; Lusinchi, X.; Meunier, B.; Pascard, C. Nouv. J. Chim. 1980, 4, 369-375. Jaouen, G.; Top, S.; Laconi, A.; Couturier, D.; Brocard, J. J. Am. Chem. Soc. 1984, 706, 2207-2208. Top, S.; Vessieres, A.; Abjean, J.-P.; Jaouen, G. J. Chem. Soc., Chem. Commun. 1984, 428-429. (e) Blagg, J.; Davies, S. G. J. Chem. Soc., Chem. Commun. 1985, 653-654. (f) Jaouen, G. Pure Appl. Chem. 1986, 58, 597-616. (g) Mathews, N.; Sainsbury, M. J. Chem. Res., Synop. 1988, 82-83. (h) Davies, S. G.; Goodfellow, C. L. J. Organomet. Chem. 1989, 370, C5-C8. Coote, S. J.; Davies, S. G.; Goodfellow, C. L.; Sutton, K. H.; Middlemiss, D.; Naylor, A. Tetrahedron: Asymmetry 1990, 1, 817-842. (j) Persson, M.; Hacksell, U. J. Chem. Soc., Perkin Trans, 1 1992, 131-135. (k) Davies, S. G.; Goodfellow, C. L.; Sutton, K. H. Tetrahedron: Asymmetry 1992, 3, 1303-1316. (l) Uemura, M.; Miyake, R.; Nakayama, K.; Shiro, M.; Hayashi, Y. J. Org. Chem. 1993, 58, 1238-1244.
12. For articles dealing with benzylic alkylation of tricarbonylchromium complexes, see: (a) Simonneaux, G.; Jaouen, G. Tetrahedron 1979, 35, 2249-2254. (b) Arzeno, H. B.; Barton, D. H. R.; Davies, S. G.; Lusinchi, X.; Meunier, B.; Pascard, C. Nouv. J. Chim. 1980, 4, 369-375. Jaouen, G.; Top, S.; Laconi, A.; Couturier, D.; Brocard, J. J. Am. Chem. Soc. 1984, 706, 2207-2208. Top, S.; Vessieres, A.; Abjean, J.-P.; Jaouen, G. J. Chem. Soc., Chem. Commun. 1984, 428-429. (e) Blagg, J.; Davies, S. G. J. Chem. Soc., Chem. Commun. 1985, 653-654. (f) Jaouen, G. Pure Appl. Chem. 1986, 58, 597-616. (g) Mathews, N.; Sainsbury, M. J. Chem. Res., Synop. 1988, 82-83. (h) Davies, S. G.; Goodfellow, C. L. J. Organomet. Chem. 1989, 370, C5-C8. Coote, S. J.; Davies, S. G.; Goodfellow, C. L.; Sutton, K. H.; Middlemiss, D.; Naylor, A. Tetrahedron: Asymmetry 1990, 1, 817-842. (j) Persson, M.; Hacksell, U. J. Chem. Soc., Perkin Trans, 1 1992, 131-135. (k) Davies, S. G.; Goodfellow, C. L.; Sutton, K. H. Tetrahedron: Asymmetry 1992, 3, 1303-1316. (l) Uemura, M.; Miyake, R.; Nakayama, K.; Shiro, M.; Hayashi, Y. J. Org. Chem. 1993, 58, 1238-1244.
13. For articles dealing with benzylic alkylation of tricarbonylchromium complexes, see: (a) Simonneaux, G.; Jaouen, G. Tetrahedron 1979, 35, 2249-2254. (b) Arzeno, H. B.; Barton, D. H. R.; Davies, S. G.; Lusinchi, X.; Meunier, B.; Pascard, C. Nouv. J. Chim. 1980, 4, 369-375. Jaouen, G.; Top, S.; Laconi, A.; Couturier, D.; Brocard, J. J. Am. Chem. Soc. 1984, 706, 2207-2208. Top, S.; Vessieres, A.; Abjean, J.-P.; Jaouen, G. J. Chem. Soc., Chem. Commun. 1984, 428-429. (e) Blagg, J.; Davies, S. G. J. Chem. Soc., Chem. Commun. 1985, 653-654. (f) Jaouen, G. Pure Appl. Chem. 1986, 58, 597-616. (g) Mathews, N.; Sainsbury, M. J. Chem. Res., Synop. 1988, 82-83. (h) Davies, S. G.; Goodfellow, C. L. J. Organomet. Chem. 1989, 370, C5-C8. Coote, S. J.; Davies, S. G.; Goodfellow, C. L.; Sutton, K. H.; Middlemiss, D.; Naylor, A. Tetrahedron: Asymmetry 1990, 1, 817-842. (j) Persson, M.; Hacksell, U. J. Chem. Soc., Perkin Trans, 1 1992, 131-135. (k) Davies, S. G.; Goodfellow, C. L.; Sutton, K. H. Tetrahedron: Asymmetry 1992, 3, 1303-1316. (l) Uemura, M.; Miyake, R.; Nakayama, K.; Shiro, M.; Hayashi, Y. J. Org. Chem. 1993, 58, 1238-1244.
14. For articles dealing with benzylic alkylation of tricarbonylchromium complexes, see: (a) Simonneaux, G.; Jaouen, G. Tetrahedron 1979, 35, 2249-2254. (b) Arzeno, H. B.; Barton, D. H. R.; Davies, S. G.; Lusinchi, X.; Meunier, B.; Pascard, C. Nouv. J. Chim. 1980, 4, 369-375. Jaouen, G.; Top, S.; Laconi, A.; Couturier, D.; Brocard, J. J. Am. Chem. Soc. 1984, 706, 2207-2208. Top, S.; Vessieres, A.; Abjean, J.-P.; Jaouen, G. J. Chem. Soc., Chem. Commun. 1984, 428-429. (e) Blagg, J.; Davies, S. G. J. Chem. Soc., Chem. Commun. 1985, 653-654. (f) Jaouen, G. Pure Appl. Chem. 1986, 58, 597-616. (g) Mathews, N.; Sainsbury, M. J. Chem. Res., Synop. 1988, 82-83. (h) Davies, S. G.; Goodfellow, C. L. J. Organomet. Chem. 1989, 370, C5-C8. Coote, S. J.; Davies, S. G.; Goodfellow, C. L.; Sutton, K. H.; Middlemiss, D.; Naylor, A. Tetrahedron: Asymmetry 1990, 1, 817-842. (j) Persson, M.; Hacksell, U. J. Chem. Soc., Perkin Trans, 1 1992, 131-135. (k) Davies, S. G.; Goodfellow, C. L.; Sutton, K. H. Tetrahedron: Asymmetry 1992, 3, 1303-1316. (l) Uemura, M.; Miyake, R.; Nakayama, K.; Shiro, M.; Hayashi, Y. J. Org. Chem. 1993, 58, 1238-1244.
15. For articles dealing with benzylic alkylation of tricarbonylchromium complexes, see: (a) Simonneaux, G.; Jaouen, G. Tetrahedron 1979, 35, 2249-2254. (b) Arzeno, H. B.; Barton, D. H. R.; Davies, S. G.; Lusinchi, X.; Meunier, B.; Pascard, C. Nouv. J. Chim. 1980, 4, 369-375. Jaouen, G.; Top, S.; Laconi, A.; Couturier, D.; Brocard, J. J. Am. Chem. Soc. 1984, 706, 2207-2208. Top, S.; Vessieres, A.; Abjean, J.-P.; Jaouen, G. J. Chem. Soc., Chem. Commun. 1984, 428-429. (e) Blagg, J.; Davies, S. G. J. Chem. Soc., Chem. Commun. 1985, 653-654. (f) Jaouen, G. Pure Appl. Chem. 1986, 58, 597-616. (g) Mathews, N.; Sainsbury, M. J. Chem. Res., Synop. 1988, 82-83. (h) Davies, S. G.; Goodfellow, C. L. J. Organomet. Chem. 1989, 370, C5-C8. Coote, S. J.; Davies, S. G.; Goodfellow, C. L.; Sutton, K. H.; Middlemiss, D.; Naylor, A. Tetrahedron: Asymmetry 1990, 1, 817-842. (j) Persson, M.; Hacksell, U. J. Chem. Soc., Perkin Trans, 1 1992, 131-135. (k) Davies, S. G.; Goodfellow, C. L.; Sutton, K. H. Tetrahedron: Asymmetry 1992, 3, 1303-1316. (l) Uemura, M.; Miyake, R.; Nakayama, K.; Shiro, M.; Hayashi, Y. J. Org. Chem. 1993, 58, 1238-1244.
16. For articles dealing with benzylic alkylation of tricarbonylchromium complexes, see: (a) Simonneaux, G.; Jaouen, G. Tetrahedron 1979, 35, 2249-2254. (b) Arzeno, H. B.; Barton, D. H. R.; Davies, S. G.; Lusinchi, X.; Meunier, B.; Pascard, C. Nouv. J. Chim. 1980, 4, 369-375. Jaouen, G.; Top, S.; Laconi, A.; Couturier, D.; Brocard, J. J. Am. Chem. Soc. 1984, 706, 2207-2208. Top, S.; Vessieres, A.; Abjean, J.-P.; Jaouen, G. J. Chem. Soc., Chem. Commun. 1984, 428-429. (e) Blagg, J.; Davies, S. G. J. Chem. Soc., Chem. Commun. 1985, 653-654. (f) Jaouen, G. Pure Appl. Chem. 1986, 58, 597-616. (g) Mathews, N.; Sainsbury, M. J. Chem. Res., Synop. 1988, 82-83. (h) Davies, S. G.; Goodfellow, C. L. J. Organomet. Chem. 1989, 370, C5-C8. Coote, S. J.; Davies, S. G.; Goodfellow, C. L.; Sutton, K. H.; Middlemiss, D.; Naylor, A. Tetrahedron: Asymmetry 1990, 1, 817-842. (j) Persson, M.; Hacksell, U. J. Chem. Soc., Perkin Trans, 1 1992, 131-135. (k) Davies, S. G.; Goodfellow, C. L.; Sutton, K. H. Tetrahedron: Asymmetry 1992, 3, 1303-1316. (l) Uemura, M.; Miyake, R.; Nakayama, K.; Shiro, M.; Hayashi, Y. J. Org. Chem. 1993, 58, 1238-1244.
17. For articles dealing with benzylic alkylation of tricarbonylchromium complexes, see: (a) Simonneaux, G.; Jaouen, G. Tetrahedron 1979, 35, 2249-2254. (b) Arzeno, H. B.; Barton, D. H. R.; Davies, S. G.; Lusinchi, X.; Meunier, B.; Pascard, C. Nouv. J. Chim. 1980, 4, 369-375. Jaouen, G.; Top, S.; Laconi, A.; Couturier, D.; Brocard, J. J. Am. Chem. Soc. 1984, 706, 2207-2208. Top, S.; Vessieres, A.; Abjean, J.-P.; Jaouen, G. J. Chem. Soc., Chem. Commun. 1984, 428-429. (e) Blagg, J.; Davies, S. G. J. Chem. Soc., Chem. Commun. 1985, 653-654. (f) Jaouen, G. Pure Appl. Chem. 1986, 58, 597-616. (g) Mathews, N.; Sainsbury, M. J. Chem. Res., Synop. 1988, 82-83. (h) Davies, S. G.; Goodfellow, C. L. J. Organomet. Chem. 1989, 370, C5-C8. Coote, S. J.; Davies, S. G.; Goodfellow, C. L.; Sutton, K. H.; Middlemiss, D.; Naylor, A. Tetrahedron: Asymmetry 1990, 1, 817-842. (j) Persson, M.; Hacksell, U. J. Chem. Soc., Perkin Trans, 1 1992, 131-135. (k) Davies, S. G.; Goodfellow, C. L.; Sutton, K. H. Tetrahedron: Asymmetry 1992, 3, 1303-1316. (l) Uemura, M.; Miyake, R.; Nakayama, K.; Shiro, M.; Hayashi, Y. J. Org. Chem. 1993, 58, 1238-1244.
18. Persson, M.; Hacksell, U.; Csöregh, I. J. Chem. Soc., Perkin Trans. 1 1991, 1453-1459.
19. The products are analogues of the pharmacologically interesting (1S,2R)-AJ76 and (1S,2R)-UH232. Johansson, A. M.; Arvidsson, L.-E.; Hacksell, U.; Nilsson, J. L. G.; Svensson, K.; Hjorth, S.; Clark, D.; Carlsson, A.; Sanchez, D.; Andersson, B.; Wikström, H. J. Med. Chem. 1985, 28, 1049-1053. equation presented (lS,2R)-AJ76: R=H (1S,2R)-UH232: R=Pr
20. The racemate has been synthesized previously: Podona, T.; Guardiola-Lemaître, B.; Caignard, D.-H.; Adam, G.; Pfeiffer, B.; Renard, P.; Guillaumet, G. J. Med. Chem. 1994, 37, 1779-1793.
21. Throughout this paper, the exo and endo nomenclature is used to denote the stereochemical relationship between the tricarbonylchromium tripod and the 2-(dipropylamino) substituent.
22. Sarda, N.; Grouiller, A.; Pacheco, H. Acad Sci., Ser. C 1974 281-284.
23. (a) Sarda, N.; Grouiller, A.; Pacheco, H. Tetrahedron Lett. 1976 4, 271-272.
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26. (b) Usse, S.; Guillaumet, G.; Viaud, M.-C. Tetrahedron Lett. 1997, 38 5501-5502.
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28. An interesting feature of the aromatic ring is that C-6 and C-8a deviate from the least-squares plane of the aromatic ring by as much as 0.026(4) and 0.035(2) A, respectively. They are positioned away from the tricarbonylchromium moiety. The tricarbonylchromium tripod is positioned slightly excentric above the aromatic ring. The distance between a perpendicular projection of Cr on the aromatic least-squares plane and the ring centroide is 0.059 Å toward C-5. The three CO groups are approximately eclipsed with carbon atoms C-5, C-7, and C-8a. This conformation of the tricarbonylchromium tripod is expected because it has previously been observed that tricarbonylchromium Prefers to be oriented eclipsed with electron-donating groups, such as alkoxy groups: see Hunter, A. D.; Mozol, V.; Tsai, S. D. Organometallics 1992, 11, 2251-2262.
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33. 8b The tetrahydropyran ring adopts a half-chair conformation that is slightly more twisted than that observed for exo-(3R)-5•HCl.
34. Ward D. E.; Rhee C. k. Tetrahedron Lett. 1991, 32, 7165-7166.