Investigation of a New Family of Chiral Ligands for Enantioselective Catalysis via Parallel Synthesis and High-Throughput Screening

Journal of Organic Chemistry

Volumn 63, Issue 16, 1998, Pages 5312-5313

  Gennari, Cesare ^a   Ceccarelli, Simona ^a   Piarulli, Umberto ^a   Montalbetti, Christian A G N ^b   Jackson, Richard F W ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000684017     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980890p     Document Type: Article

References (49)

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16. For research papers, see: (a) Menger, F. M.; Eliseev, A. V.; Migulin, V. A. J. Org. Chem. 1995, 60, 6666. (b) Menger, F. M.; West, C. A.; Ding, J. Chem. Commun. 1997, 633. (c) Taylor, S. J.; Merken, J. P. Science 1998, 280, 267. (d) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (e) Burgess, K.; Lim, H.; Porte, G.; Sulikowski, G. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 220. (f) Gilbertson, S. R.; Wang, X. Tetrahedron Lett. 1996, 37, 6475. (g) Gilbertson, S. R.; Chang, C. T. Chem. Commun. 1997, 975. (h) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668. (i) Shimizu, K. D.; Cole, B. M.; Krueger, C. A.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1704. (j) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
17. For research papers, see: (a) Menger, F. M.; Eliseev, A. V.; Migulin, V. A. J. Org. Chem. 1995, 60, 6666. (b) Menger, F. M.; West, C. A.; Ding, J. Chem. Commun. 1997, 633. (c) Taylor, S. J.; Merken, J. P. Science 1998, 280, 267. (d) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (e) Burgess, K.; Lim, H.; Porte, G.; Sulikowski, G. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 220. (f) Gilbertson, S. R.; Wang, X. Tetrahedron Lett. 1996, 37, 6475. (g) Gilbertson, S. R.; Chang, C. T. Chem. Commun. 1997, 975. (h) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668. (i) Shimizu, K. D.; Cole, B. M.; Krueger, C. A.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1704. (j) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
18. For research papers, see: (a) Menger, F. M.; Eliseev, A. V.; Migulin, V. A. J. Org. Chem. 1995, 60, 6666. (b) Menger, F. M.; West, C. A.; Ding, J. Chem. Commun. 1997, 633. (c) Taylor, S. J.; Merken, J. P. Science 1998, 280, 267. (d) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (e) Burgess, K.; Lim, H.; Porte, G.; Sulikowski, G. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 220. (f) Gilbertson, S. R.; Wang, X. Tetrahedron Lett. 1996, 37, 6475. (g) Gilbertson, S. R.; Chang, C. T. Chem. Commun. 1997, 975. (h) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668. (i) Shimizu, K. D.; Cole, B. M.; Krueger, C. A.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1704. (j) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
19. For research papers, see: (a) Menger, F. M.; Eliseev, A. V.; Migulin, V. A. J. Org. Chem. 1995, 60, 6666. (b) Menger, F. M.; West, C. A.; Ding, J. Chem. Commun. 1997, 633. (c) Taylor, S. J.; Merken, J. P. Science 1998, 280, 267. (d) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (e) Burgess, K.; Lim, H.; Porte, G.; Sulikowski, G. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 220. (f) Gilbertson, S. R.; Wang, X. Tetrahedron Lett. 1996, 37, 6475. (g) Gilbertson, S. R.; Chang, C. T. Chem. Commun. 1997, 975. (h) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668. (i) Shimizu, K. D.; Cole, B. M.; Krueger, C. A.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1704. (j) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
20. For research papers, see: (a) Menger, F. M.; Eliseev, A. V.; Migulin, V. A. J. Org. Chem. 1995, 60, 6666. (b) Menger, F. M.; West, C. A.; Ding, J. Chem. Commun. 1997, 633. (c) Taylor, S. J.; Merken, J. P. Science 1998, 280, 267. (d) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (e) Burgess, K.; Lim, H.; Porte, G.; Sulikowski, G. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 220. (f) Gilbertson, S. R.; Wang, X. Tetrahedron Lett. 1996, 37, 6475. (g) Gilbertson, S. R.; Chang, C. T. Chem. Commun. 1997, 975. (h) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668. (i) Shimizu, K. D.; Cole, B. M.; Krueger, C. A.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1704. (j) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
21. For research papers, see: (a) Menger, F. M.; Eliseev, A. V.; Migulin, V. A. J. Org. Chem. 1995, 60, 6666. (b) Menger, F. M.; West, C. A.; Ding, J. Chem. Commun. 1997, 633. (c) Taylor, S. J.; Merken, J. P. Science 1998, 280, 267. (d) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (e) Burgess, K.; Lim, H.; Porte, G.; Sulikowski, G. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 220. (f) Gilbertson, S. R.; Wang, X. Tetrahedron Lett. 1996, 37, 6475. (g) Gilbertson, S. R.; Chang, C. T. Chem. Commun. 1997, 975. (h) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668. (i) Shimizu, K. D.; Cole, B. M.; Krueger, C. A.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1704. (j) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
22. For research papers, see: (a) Menger, F. M.; Eliseev, A. V.; Migulin, V. A. J. Org. Chem. 1995, 60, 6666. (b) Menger, F. M.; West, C. A.; Ding, J. Chem. Commun. 1997, 633. (c) Taylor, S. J.; Merken, J. P. Science 1998, 280, 267. (d) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (e) Burgess, K.; Lim, H.; Porte, G.; Sulikowski, G. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 220. (f) Gilbertson, S. R.; Wang, X. Tetrahedron Lett. 1996, 37, 6475. (g) Gilbertson, S. R.; Chang, C. T. Chem. Commun. 1997, 975. (h) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668. (i) Shimizu, K. D.; Cole, B. M.; Krueger, C. A.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1704. (j) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
23. For research papers, see: (a) Menger, F. M.; Eliseev, A. V.; Migulin, V. A. J. Org. Chem. 1995, 60, 6666. (b) Menger, F. M.; West, C. A.; Ding, J. Chem. Commun. 1997, 633. (c) Taylor, S. J.; Merken, J. P. Science 1998, 280, 267. (d) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (e) Burgess, K.; Lim, H.; Porte, G.; Sulikowski, G. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 220. (f) Gilbertson, S. R.; Wang, X. Tetrahedron Lett. 1996, 37, 6475. (g) Gilbertson, S. R.; Chang, C. T. Chem. Commun. 1997, 975. (h) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668. (i) Shimizu, K. D.; Cole, B. M.; Krueger, C. A.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1704. (j) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
24. For research papers, see: (a) Menger, F. M.; Eliseev, A. V.; Migulin, V. A. J. Org. Chem. 1995, 60, 6666. (b) Menger, F. M.; West, C. A.; Ding, J. Chem. Commun. 1997, 633. (c) Taylor, S. J.; Merken, J. P. Science 1998, 280, 267. (d) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712. (e) Burgess, K.; Lim, H.; Porte, G.; Sulikowski, G. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 220. (f) Gilbertson, S. R.; Wang, X. Tetrahedron Lett. 1996, 37, 6475. (g) Gilbertson, S. R.; Chang, C. T. Chem. Commun. 1997, 975. (h) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668. (i) Shimizu, K. D.; Cole, B. M.; Krueger, C. A.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1704. (j) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
25. 2Zn additions to aldehydes, see: (a) Takahashi, H.; Kawakita, T.; Yoshioka, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 7095. (b) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. (c) Zhang, X.; Guo, C. Tetrahedron Lett. 1995, 36, 4947. (d) Lutz, C.; Knochel, P. J. Org. Chem. 1997, 62, 7895. (e) Ramón, D. J.; Yus, M. Tetrahedron: Asymmetry 1997, 8, 2479. (f) Cernerud, M.; Skrinning, A.; Bérgère, I.; Moberg, C. Tetrahedron: Asymmetry 1997, 8, 3437. (g) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 510. For cyclopropanation reactions, see: (h) Takahashi, H.; Yoshioka, M.; Shibasaki, M.; Ohno, M.; Imai, N.; Kobayashi, S. Tetrahedron 1995, 51, 12013 and references therein, (i) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 584. (j) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 3390 and references therein, (k) Imai, N.; Sakamoto, K.; Maeda, M.; Kouge, K.; Yoshizane, K.; Nokami, J. Tetrahedron Lett. 1997, 38, 1423.
26. 2Zn additions to aldehydes, see: (a) Takahashi, H.; Kawakita, T.; Yoshioka, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 7095. (b) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. (c) Zhang, X.; Guo, C. Tetrahedron Lett. 1995, 36, 4947. (d) Lutz, C.; Knochel, P. J. Org. Chem. 1997, 62, 7895. (e) Ramón, D. J.; Yus, M. Tetrahedron: Asymmetry 1997, 8, 2479. (f) Cernerud, M.; Skrinning, A.; Bérgère, I.; Moberg, C. Tetrahedron: Asymmetry 1997, 8, 3437. (g) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 510. For cyclopropanation reactions, see: (h) Takahashi, H.; Yoshioka, M.; Shibasaki, M.; Ohno, M.; Imai, N.; Kobayashi, S. Tetrahedron 1995, 51, 12013 and references therein, (i) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 584. (j) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 3390 and references therein, (k) Imai, N.; Sakamoto, K.; Maeda, M.; Kouge, K.; Yoshizane, K.; Nokami, J. Tetrahedron Lett. 1997, 38, 1423.
27. 2Zn additions to aldehydes, see: (a) Takahashi, H.; Kawakita, T.; Yoshioka, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 7095. (b) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. (c) Zhang, X.; Guo, C. Tetrahedron Lett. 1995, 36, 4947. (d) Lutz, C.; Knochel, P. J. Org. Chem. 1997, 62, 7895. (e) Ramón, D. J.; Yus, M. Tetrahedron: Asymmetry 1997, 8, 2479. (f) Cernerud, M.; Skrinning, A.; Bérgère, I.; Moberg, C. Tetrahedron: Asymmetry 1997, 8, 3437. (g) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 510. For cyclopropanation reactions, see: (h) Takahashi, H.; Yoshioka, M.; Shibasaki, M.; Ohno, M.; Imai, N.; Kobayashi, S. Tetrahedron 1995, 51, 12013 and references therein, (i) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 584. (j) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 3390 and references therein, (k) Imai, N.; Sakamoto, K.; Maeda, M.; Kouge, K.; Yoshizane, K.; Nokami, J. Tetrahedron Lett. 1997, 38, 1423.
28. 2Zn additions to aldehydes, see: (a) Takahashi, H.; Kawakita, T.; Yoshioka, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 7095. (b) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. (c) Zhang, X.; Guo, C. Tetrahedron Lett. 1995, 36, 4947. (d) Lutz, C.; Knochel, P. J. Org. Chem. 1997, 62, 7895. (e) Ramón, D. J.; Yus, M. Tetrahedron: Asymmetry 1997, 8, 2479. (f) Cernerud, M.; Skrinning, A.; Bérgère, I.; Moberg, C. Tetrahedron: Asymmetry 1997, 8, 3437. (g) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 510. For cyclopropanation reactions, see: (h) Takahashi, H.; Yoshioka, M.; Shibasaki, M.; Ohno, M.; Imai, N.; Kobayashi, S. Tetrahedron 1995, 51, 12013 and references therein, (i) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 584. (j) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 3390 and references therein, (k) Imai, N.; Sakamoto, K.; Maeda, M.; Kouge, K.; Yoshizane, K.; Nokami, J. Tetrahedron Lett. 1997, 38, 1423.
29. 2Zn additions to aldehydes, see: (a) Takahashi, H.; Kawakita, T.; Yoshioka, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 7095. (b) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. (c) Zhang, X.; Guo, C. Tetrahedron Lett. 1995, 36, 4947. (d) Lutz, C.; Knochel, P. J. Org. Chem. 1997, 62, 7895. (e) Ramón, D. J.; Yus, M. Tetrahedron: Asymmetry 1997, 8, 2479. (f) Cernerud, M.; Skrinning, A.; Bérgère, I.; Moberg, C. Tetrahedron: Asymmetry 1997, 8, 3437. (g) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 510. For cyclopropanation reactions, see: (h) Takahashi, H.; Yoshioka, M.; Shibasaki, M.; Ohno, M.; Imai, N.; Kobayashi, S. Tetrahedron 1995, 51, 12013 and references therein, (i) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 584. (j) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 3390 and references therein, (k) Imai, N.; Sakamoto, K.; Maeda, M.; Kouge, K.; Yoshizane, K.; Nokami, J. Tetrahedron Lett. 1997, 38, 1423.
30. 2Zn additions to aldehydes, see: (a) Takahashi, H.; Kawakita, T.; Yoshioka, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 7095. (b) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. (c) Zhang, X.; Guo, C. Tetrahedron Lett. 1995, 36, 4947. (d) Lutz, C.; Knochel, P. J. Org. Chem. 1997, 62, 7895. (e) Ramón, D. J.; Yus, M. Tetrahedron: Asymmetry 1997, 8, 2479. (f) Cernerud, M.; Skrinning, A.; Bérgère, I.; Moberg, C. Tetrahedron: Asymmetry 1997, 8, 3437. (g) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 510. For cyclopropanation reactions, see: (h) Takahashi, H.; Yoshioka, M.; Shibasaki, M.; Ohno, M.; Imai, N.; Kobayashi, S. Tetrahedron 1995, 51, 12013 and references therein, (i) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 584. (j) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 3390 and references therein, (k) Imai, N.; Sakamoto, K.; Maeda, M.; Kouge, K.; Yoshizane, K.; Nokami, J. Tetrahedron Lett. 1997, 38, 1423.
31. 2Zn additions to aldehydes, see: (a) Takahashi, H.; Kawakita, T.; Yoshioka, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 7095. (b) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. (c) Zhang, X.; Guo, C. Tetrahedron Lett. 1995, 36, 4947. (d) Lutz, C.; Knochel, P. J. Org. Chem. 1997, 62, 7895. (e) Ramón, D. J.; Yus, M. Tetrahedron: Asymmetry 1997, 8, 2479. (f) Cernerud, M.; Skrinning, A.; Bérgère, I.; Moberg, C. Tetrahedron: Asymmetry 1997, 8, 3437. (g) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 510. For cyclopropanation reactions, see: (h) Takahashi, H.; Yoshioka, M.; Shibasaki, M.; Ohno, M.; Imai, N.; Kobayashi, S. Tetrahedron 1995, 51, 12013 and references therein, (i) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 584. (j) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 3390 and references therein, (k) Imai, N.; Sakamoto, K.; Maeda, M.; Kouge, K.; Yoshizane, K.; Nokami, J. Tetrahedron Lett. 1997, 38, 1423.
32. 2Zn additions to aldehydes, see: (a) Takahashi, H.; Kawakita, T.; Yoshioka, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 7095. (b) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. (c) Zhang, X.; Guo, C. Tetrahedron Lett. 1995, 36, 4947. (d) Lutz, C.; Knochel, P. J. Org. Chem. 1997, 62, 7895. (e) Ramón, D. J.; Yus, M. Tetrahedron: Asymmetry 1997, 8, 2479. (f) Cernerud, M.; Skrinning, A.; Bérgère, I.; Moberg, C. Tetrahedron: Asymmetry 1997, 8, 3437. (g) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 510. For cyclopropanation reactions, see: (h) Takahashi, H.; Yoshioka, M.; Shibasaki, M.; Ohno, M.; Imai, N.; Kobayashi, S. Tetrahedron 1995, 51, 12013 and references therein, (i) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 584. (j) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 3390 and references therein, (k) Imai, N.; Sakamoto, K.; Maeda, M.; Kouge, K.; Yoshizane, K.; Nokami, J. Tetrahedron Lett. 1997, 38, 1423.
33. 2Zn additions to aldehydes, see: (a) Takahashi, H.; Kawakita, T.; Yoshioka, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 7095. (b) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. (c) Zhang, X.; Guo, C. Tetrahedron Lett. 1995, 36, 4947. (d) Lutz, C.; Knochel, P. J. Org. Chem. 1997, 62, 7895. (e) Ramón, D. J.; Yus, M. Tetrahedron: Asymmetry 1997, 8, 2479. (f) Cernerud, M.; Skrinning, A.; Bérgère, I.; Moberg, C. Tetrahedron: Asymmetry 1997, 8, 3437. (g) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 510. For cyclopropanation reactions, see: (h) Takahashi, H.; Yoshioka, M.; Shibasaki, M.; Ohno, M.; Imai, N.; Kobayashi, S. Tetrahedron 1995, 51, 12013 and references therein, (i) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 584. (j) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 3390 and references therein, (k) Imai, N.; Sakamoto, K.; Maeda, M.; Kouge, K.; Yoshizane, K.; Nokami, J. Tetrahedron Lett. 1997, 38, 1423.
34. 2Zn additions to aldehydes, see: (a) Takahashi, H.; Kawakita, T.; Yoshioka, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 7095. (b) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691. (c) Zhang, X.; Guo, C. Tetrahedron Lett. 1995, 36, 4947. (d) Lutz, C.; Knochel, P. J. Org. Chem. 1997, 62, 7895. (e) Ramón, D. J.; Yus, M. Tetrahedron: Asymmetry 1997, 8, 2479. (f) Cernerud, M.; Skrinning, A.; Bérgère, I.; Moberg, C. Tetrahedron: Asymmetry 1997, 8, 3437. (g) Halm, C.; Kurth, M. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 510. For cyclopropanation reactions, see: (h) Takahashi, H.; Yoshioka, M.; Shibasaki, M.; Ohno, M.; Imai, N.; Kobayashi, S. Tetrahedron 1995, 51, 12013 and references therein, (i) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 584. (j) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 3390 and references therein, (k) Imai, N.; Sakamoto, K.; Maeda, M.; Kouge, K.; Yoshizane, K.; Nokami, J. Tetrahedron Lett. 1997, 38, 1423.
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