Chiral auxiliaries, ligands and arene chromium complexes

Pure and Applied Chemistry

Volumn 69, Issue 3, 1997, Pages 543-546

  Kundig E P ^a   Amurrio, D ^a   Anderson, G ^a   Beruben, D ^a   Khan, K ^a   Ripa, A ^a   Ronggang, L ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038401539     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199769030543     Document Type: Article

References (32)

1. E. P. Kündig, A. Ripa, R. Liu and G. Bernardinelli, J. Org. Chem. 1994, 59, 4773.
2. For a review see: M. F. Semmelhack in Comprehensive Organometallic Chemistry II, Vol. 12 (Eds.: E. Abel, G. Stone, G. Wilkinson), p. 979, Pergamon Press, Oxford (1995).
3. E. P. Kündig, A. Ripa, R. Liu, D. Amurrio and G. Bernardinelli, Organometallics, 1993, 12, 3724.
4. For a review see: a) B. Giese, B. Kopping, T. Göbel, J. Dickhaut, G. Thoma, K.J. Kulicke and F. Trach, Organic Reactions, 1996, 48, 301; selected references: b) R. Stork and R. Mook, Jr., J. Am. Chem. Soc., 1983, 105, 3720; N. N. Marinovic and H. Ramanathan, Tetrahedron Lett., 1983, 24, 1871; K. Nozaki, K. Oshima and K. Utimoto, J. Am. Chem. Soc., 1987, 109, 2547; e) M. J. Begley, M. Ladlow and G. J. Pattenden, J. Chem. Soc., Perkin Trans 1, 1988, 1095; f) D. P. Curran, Synthesis, 1988, 417 and 489; g) M. Journet, W. Smadja and M. Malacria, Synlett., 1990, 320; h) C. P. Jasperse, D. P. Curran and T. L. Feving, Chem. Rev., 1991, 91, 1237.
5. For a review see: a) B. Giese, B. Kopping, T. Göbel, J. Dickhaut, G. Thoma, K.J. Kulicke and F. Trach, Organic Reactions, 1996, 48, 301; selected references: b) R. Stork and R. Mook, Jr., J. Am. Chem. Soc., 1983, 105, 3720; N. N. Marinovic and H. Ramanathan, Tetrahedron Lett., 1983, 24, 1871; K. Nozaki, K. Oshima and K. Utimoto, J. Am. Chem. Soc., 1987, 109, 2547; e) M. J. Begley, M. Ladlow and G. J. Pattenden, J. Chem. Soc., Perkin Trans 1, 1988, 1095; f) D. P. Curran, Synthesis, 1988, 417 and 489; g) M. Journet, W. Smadja and M. Malacria, Synlett., 1990, 320; h) C. P. Jasperse, D. P. Curran and T. L. Feving, Chem. Rev., 1991, 91, 1237.
6. For a review see: a) B. Giese, B. Kopping, T. Göbel, J. Dickhaut, G. Thoma, K.J. Kulicke and F. Trach, Organic Reactions, 1996, 48, 301; selected references: b) R. Stork and R. Mook, Jr., J. Am. Chem. Soc., 1983, 105, 3720; c) N. N. Marinovic and H. Ramanathan, Tetrahedron Lett., 1983, 24, 1871; K. Nozaki, K. Oshima and K. Utimoto, J. Am. Chem. Soc., 1987, 109, 2547; e) M. J. Begley, M. Ladlow and G. J. Pattenden, J. Chem. Soc., Perkin Trans 1, 1988, 1095; f) D. P. Curran, Synthesis, 1988, 417 and 489; g) M. Journet, W. Smadja and M. Malacria, Synlett., 1990, 320; h) C. P. Jasperse, D. P. Curran and T. L. Feving, Chem. Rev., 1991, 91, 1237.
7. For a review see: a) B. Giese, B. Kopping, T. Göbel, J. Dickhaut, G. Thoma, K.J. Kulicke and F. Trach, Organic Reactions, 1996, 48, 301; selected references: b) R. Stork and R. Mook, Jr., J. Am. Chem. Soc., 1983, 105, 3720; N. N. Marinovic and H. Ramanathan, Tetrahedron Lett., 1983, 24, 1871; d) K. Nozaki, K. Oshima and K. Utimoto, J. Am. Chem. Soc., 1987, 109, 2547; e) M. J. Begley, M. Ladlow and G. J. Pattenden, J. Chem. Soc., Perkin Trans 1, 1988, 1095; f) D. P. Curran, Synthesis, 1988, 417 and 489; g) M. Journet, W. Smadja and M. Malacria, Synlett., 1990, 320; h) C. P. Jasperse, D. P. Curran and T. L. Feving, Chem. Rev., 1991, 91, 1237.
8. For a review see: a) B. Giese, B. Kopping, T. Göbel, J. Dickhaut, G. Thoma, K.J. Kulicke and F. Trach, Organic Reactions, 1996, 48, 301; selected references: b) R. Stork and R. Mook, Jr., J. Am. Chem. Soc., 1983, 105, 3720; N. N. Marinovic and H. Ramanathan, Tetrahedron Lett., 1983, 24, 1871; K. Nozaki, K. Oshima and K. Utimoto, J. Am. Chem. Soc., 1987, 109, 2547; e) M. J. Begley, M. Ladlow and G. J. Pattenden, J. Chem. Soc., Perkin Trans 1, 1988, 1095; f) D. P. Curran, Synthesis, 1988, 417 and 489; g) M. Journet, W. Smadja and M. Malacria, Synlett., 1990, 320; h) C. P. Jasperse, D. P. Curran and T. L. Feving, Chem. Rev., 1991, 91, 1237.
9. For a review see: a) B. Giese, B. Kopping, T. Göbel, J. Dickhaut, G. Thoma, K.J. Kulicke and F. Trach, Organic Reactions, 1996, 48, 301; selected references: b) R. Stork and R. Mook, Jr., J. Am. Chem. Soc., 1983, 105, 3720; N. N. Marinovic and H. Ramanathan, Tetrahedron Lett., 1983, 24, 1871; K. Nozaki, K. Oshima and K. Utimoto, J. Am. Chem. Soc., 1987, 109, 2547; e) M. J. Begley, M. Ladlow and G. J. Pattenden, J. Chem. Soc., Perkin Trans 1, 1988, 1095; f) D. P. Curran, Synthesis, 1988, 417 and 489; g) M. Journet, W. Smadja and M. Malacria, Synlett., 1990, 320; h) C. P. Jasperse, D. P. Curran and T. L. Feving, Chem. Rev., 1991, 91, 1237.
10. For a review see: a) B. Giese, B. Kopping, T. Göbel, J. Dickhaut, G. Thoma, K.J. Kulicke and F. Trach, Organic Reactions, 1996, 48, 301; selected references: b) R. Stork and R. Mook, Jr., J. Am. Chem. Soc., 1983, 105, 3720; N. N. Marinovic and H. Ramanathan, Tetrahedron Lett., 1983, 24, 1871; K. Nozaki, K. Oshima and K. Utimoto, J. Am. Chem. Soc., 1987, 109, 2547; e) M. J. Begley, M. Ladlow and G. J. Pattenden, J. Chem. Soc., Perkin Trans 1, 1988, 1095; f) D. P. Curran, Synthesis, 1988, 417 and 489; g) M. Journet, W. Smadja and M. Malacria, Synlett., 1990, 320; h) C. P. Jasperse, D. P. Curran and T. L. Feving, Chem. Rev., 1991, 91, 1237.
11. For a review see: a) B. Giese, B. Kopping, T. Göbel, J. Dickhaut, G. Thoma, K.J. Kulicke and F. Trach, Organic Reactions, 1996, 48, 301; selected references: b) R. Stork and R. Mook, Jr., J. Am. Chem. Soc., 1983, 105, 3720; N. N. Marinovic and H. Ramanathan, Tetrahedron Lett., 1983, 24, 1871; K. Nozaki, K. Oshima and K. Utimoto, J. Am. Chem. Soc., 1987, 109, 2547; e) M. J. Begley, M. Ladlow and G. J. Pattenden, J. Chem. Soc., Perkin Trans 1, 1988, 1095; f) D. P. Curran, Synthesis, 1988, 417 and 489; g) M. Journet, W. Smadja and M. Malacria, Synlett., 1990, 320; h) C. P. Jasperse, D. P. Curran and T. L. Feving, Chem. Rev., 1991, 91, 1237.
12. (a) L. S. Hegedus, Transition Metals in Organic Chemistry, University Science Books, Mill Valley, 1994;
13. b) J. Tsuji, Palladium Reagents and Catalysts, John Wiley & Sons, Chichester, 1995.
14. A. de Meijere and F. E. Meyer Angew. Chem. Int. Ed. 1994, 33, 2379.
15. For precedents see: a) J. Ardisson, J. P. Ferezou, M. Julia and A. Pancrazi, Tetrahedron Lett., 1987, 28, 2001; b) R. Mook, Jr. and P. M. Sher, Org. Synth., 1988, 66, 75; K. Nozaki, K. Oshima and K. Utimoto, Tetrahedron, 1989, 45, 923; K. Vijaya Bhaskar and G. S. R. Subba Rao, Tetrahedron Lett., 1989, 30, 225; e) D. P. Curran, W. Shen, J. Zhang and T. A. Heffner, J. Am. Chem. Soc., 1990, 112, 6738; f) D. L. J. Clive and H. W. Manning, J. Chem. Soc., Chem. Commun., 1993, 667; g) D. L. J. Clive and S. R. Magnuson, Tetrahedron Lett., 1995, 36, 15.
16. For precedents see: a) J. Ardisson, J. P. Ferezou, M. Julia and A. Pancrazi, Tetrahedron Lett., 1987, 28, 2001; b) R. Mook, Jr. and P. M. Sher, Org. Synth., 1988, 66, 75; K. Nozaki, K. Oshima and K. Utimoto, Tetrahedron, 1989, 45, 923; K. Vijaya Bhaskar and G. S. R. Subba Rao, Tetrahedron Lett., 1989, 30, 225; e) D. P. Curran, W. Shen, J. Zhang and T. A. Heffner, J. Am. Chem. Soc., 1990, 112, 6738; f) D. L. J. Clive and H. W. Manning, J. Chem. Soc., Chem. Commun., 1993, 667; g) D. L. J. Clive and S. R. Magnuson, Tetrahedron Lett., 1995, 36, 15.
17. For precedents see: a) J. Ardisson, J. P. Ferezou, M. Julia and A. Pancrazi, Tetrahedron Lett., 1987, 28, 2001; b) R. Mook, Jr. and P. M. Sher, Org. Synth., 1988, 66, 75; c) K. Nozaki, K. Oshima and K. Utimoto, Tetrahedron, 1989, 45, 923; K. Vijaya Bhaskar and G. S. R. Subba Rao, Tetrahedron Lett., 1989, 30, 225; e) D. P. Curran, W. Shen, J. Zhang and T. A. Heffner, J. Am. Chem. Soc., 1990, 112, 6738; f) D. L. J. Clive and H. W. Manning, J. Chem. Soc., Chem. Commun., 1993, 667; g) D. L. J. Clive and S. R. Magnuson, Tetrahedron Lett., 1995, 36, 15.
18. For precedents see: a) J. Ardisson, J. P. Ferezou, M. Julia and A. Pancrazi, Tetrahedron Lett., 1987, 28, 2001; b) R. Mook, Jr. and P. M. Sher, Org. Synth., 1988, 66, 75; K. Nozaki, K. Oshima and K. Utimoto, Tetrahedron, 1989, 45, 923; d) K. Vijaya Bhaskar and G. S. R. Subba Rao, Tetrahedron Lett., 1989, 30, 225; e) D. P. Curran, W. Shen, J. Zhang and T. A. Heffner, J. Am. Chem. Soc., 1990, 112, 6738; f) D. L. J. Clive and H. W. Manning, J. Chem. Soc., Chem. Commun., 1993, 667; g) D. L. J. Clive and S. R. Magnuson, Tetrahedron Lett., 1995, 36, 15.
19. For precedents see: a) J. Ardisson, J. P. Ferezou, M. Julia and A. Pancrazi, Tetrahedron Lett., 1987, 28, 2001; b) R. Mook, Jr. and P. M. Sher, Org. Synth., 1988, 66, 75; K. Nozaki, K. Oshima and K. Utimoto, Tetrahedron, 1989, 45, 923; K. Vijaya Bhaskar and G. S. R. Subba Rao, Tetrahedron Lett., 1989, 30, 225; e) D. P. Curran, W. Shen, J. Zhang and T. A. Heffner, J. Am. Chem. Soc., 1990, 112, 6738; f) D. L. J. Clive and H. W. Manning, J. Chem. Soc., Chem. Commun., 1993, 667; g) D. L. J. Clive and S. R. Magnuson, Tetrahedron Lett., 1995, 36, 15.
20. For precedents see: a) J. Ardisson, J. P. Ferezou, M. Julia and A. Pancrazi, Tetrahedron Lett., 1987, 28, 2001; b) R. Mook, Jr. and P. M. Sher, Org. Synth., 1988, 66, 75; K. Nozaki, K. Oshima and K. Utimoto, Tetrahedron, 1989, 45, 923; K. Vijaya Bhaskar and G. S. R. Subba Rao, Tetrahedron Lett., 1989, 30, 225; e) D. P. Curran, W. Shen, J. Zhang and T. A. Heffner, J. Am. Chem. Soc., 1990, 112, 6738; f) D. L. J. Clive and H. W. Manning, J. Chem. Soc., Chem. Commun., 1993, 667; g) D. L. J. Clive and S. R. Magnuson, Tetrahedron Lett., 1995, 36, 15.
21. For precedents see: a) J. Ardisson, J. P. Ferezou, M. Julia and A. Pancrazi, Tetrahedron Lett., 1987, 28, 2001; b) R. Mook, Jr. and P. M. Sher, Org. Synth., 1988, 66, 75; K. Nozaki, K. Oshima and K. Utimoto, Tetrahedron, 1989, 45, 923; K. Vijaya Bhaskar and G. S. R. Subba Rao, Tetrahedron Lett., 1989, 30, 225; e) D. P. Curran, W. Shen, J. Zhang and T. A. Heffner, J. Am. Chem. Soc., 1990, 112, 6738; f) D. L. J. Clive and H. W. Manning, J. Chem. Soc., Chem. Commun., 1993, 667; g) D. L. J. Clive and S. R. Magnuson, Tetrahedron Lett., 1995, 36, 15.
22. a) G. Stork and N. H. Baine, J. Am. Chem. Soc., 1982, 104, 2321 and references cited therein;
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25. D. Beruben and E.P. Kündig, Helv. Chim. Acta, 1996, 79, 0000 (in press).
26. Chiral ligands (1.): a) E. P. Kündig, A. Quattropani, M. Inage, A. Ripa, C. Dupré, A. F. Cunningham, Jr. and B. Bourdin, Pure Appl. Chem. 1996, 68, 97. Chiral auxiliaries (2.): Oxazolines: b) E.P. Kündig, A. Ripa and G. Bernardinelli. Angew. Chem. Int. Ed. Engl. 31, 1071 (1992). Hydrazones: this paper. Chiral nucleophiles (3.): D. Amurrio, K. Khan, E. P. Kündig, J. Org. Chem. 1996, 61, 2258. Diastereoselective nucleophilic additions to planar chiral complexes. Ph.D. Thesis Anna Quattropani, Geneva 1996, manuscript in preparation.
27. Chiral ligands (1.): a) E. P. Kündig, A. Quattropani, M. Inage, A. Ripa, C. Dupré, A. F. Cunningham, Jr. and B. Bourdin, Pure Appl. Chem. 1996, 68, 97. Chiral auxiliaries (2.): Oxazolines: b) E.P. Kündig, A. Ripa and G. Bernardinelli. Angew. Chem. Int. Ed. Engl. 31, 1071 (1992). Hydrazones: this paper. Chiral nucleophiles (3.): D. Amurrio, K. Khan, E. P. Kündig, J. Org. Chem. 1996, 61, 2258. Diastereoselective nucleophilic additions to planar chiral complexes. Ph.D. Thesis Anna Quattropani, Geneva 1996, manuscript in preparation.
28. Chiral ligands (1.): a) E. P. Kündig, A. Quattropani, M. Inage, A. Ripa, C. Dupré, A. F. Cunningham, Jr. and B. Bourdin, Pure Appl. Chem. 1996, 68, 97. Chiral auxiliaries (2.): Oxazolines: b) E.P. Kündig, A. Ripa and G. Bernardinelli. Angew. Chem. Int. Ed. Engl. 31, 1071 (1992). Hydrazones: this paper. Chiral nucleophiles (3.): c) D. Amurrio, K. Khan, E. P. Kündig, J. Org. Chem. 1996, 61, 2258. Diastereoselective nucleophilic additions to planar chiral complexes. Ph.D. Thesis Anna Quattropani, Geneva 1996, manuscript in preparation.
29. SAMP-hydrazone, Enders'reagent: D. Enders, M. Klatt in Encyclopedia of Reagents for Organic Synthesis, Vol 1 (Ed. L. Paquette), p. 178, John Wiley & Sons, New York (1995).
30. E. P. Kündig, R. Liu and A. Ripa, Helv. Chim. Acta. 1992, 75, 2657.
31. K. Tomioka, Synthesis 1990, 541.
32. Compared to imines, hydrazones are far more resistant to non-oxidative hydrolysis (11).