A highly chemo- and enantio-selective hetero-Diels-Alder reaction catalysed by chiral aluminium complexes

Chemical Communications

Volumn , Issue 20, 1996, Pages 2373-2374

  Graven, Anette ^a   Johannsen, Mogens ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003084885     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960002373     Document Type: Article

References (34)

1. See e.g. (a) D. L. Boger and S. M. Weinreb, in Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, New York, 1987; (b) H. B. Kagan and O. Riant, Chem. Rev., 1992, 92, 1007; H. Waldmann, Synthesis, 1994, 535.
2. See e.g. (a) D. L. Boger and S. M. Weinreb, in Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, New York, 1987; (b) H. B. Kagan and O. Riant, Chem. Rev., 1992, 92, 1007; H. Waldmann, Synthesis, 1994, 535.
3. See e.g. (a) D. L. Boger and S. M. Weinreb, in Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, New York, 1987; (b) H. B. Kagan and O. Riant, Chem. Rev., 1992, 92, 1007; H. Waldmann, Synthesis, 1994, 535.
4. See e.g. (a) K. Mikami and M. Shimizu, Chem. Rev., 1992, 92, 1021; (b) K. Mikami, Y. Motoyama and M. Terada, J. Am. Chem. Soc., 1994, 116, 2812; (c) M. Terada, K. Mikami and T. Nakai, Tetrahedron Lett., 1991, 32, 935; (d) M. Teradam and K. Mikami, J. Chem. Soc., Chem. Commun., 1995, 2391.
5. See e.g. (a) K. Mikami and M. Shimizu, Chem. Rev., 1992, 92, 1021; (b) K. Mikami, Y. Motoyama and M. Terada, J. Am. Chem. Soc., 1994, 116, 2812; (c) M. Terada, K. Mikami and T. Nakai, Tetrahedron Lett., 1991, 32, 935; (d) M. Teradam and K. Mikami, J. Chem. Soc., Chem. Commun., 1995, 2391.
6. See e.g. (a) K. Mikami and M. Shimizu, Chem. Rev., 1992, 92, 1021; (b) K. Mikami, Y. Motoyama and M. Terada, J. Am. Chem. Soc., 1994, 116, 2812; (c) M. Terada, K. Mikami and T. Nakai, Tetrahedron Lett., 1991, 32, 935; (d) M. Teradam and K. Mikami, J. Chem. Soc., Chem. Commun., 1995, 2391.
7. See e.g. (a) K. Mikami and M. Shimizu, Chem. Rev., 1992, 92, 1021; (b) K. Mikami, Y. Motoyama and M. Terada, J. Am. Chem. Soc., 1994, 116, 2812; (c) M. Terada, K. Mikami and T. Nakai, Tetrahedron Lett., 1991, 32, 935; (d) M. Teradam and K. Mikami, J. Chem. Soc., Chem. Commun., 1995, 2391.
8. M. Johannsen and K. A. Jørgensen, J. Org. Chem., 1995, 60, 5757; Tetrahedron, 1996, 52, 7321.
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12. See e.g. (a) G. E. Keck, X.-Y. Li and D. Krishanmurthy, J. Org. Chem., 1995, 60, 5998; (b) M. Quimpére and K. Jankowski, J. Chem. Soc., Chem. Commun., 1987, 676; (c) A. Togni, Organometallics, 1990, 9, 3106; (d) Y. Motoyama and K. Mikami, J. Chem. Soc., Chem. Commun., 1994, 1563; (e) Q. Gao, M. Muruyama, M. Mouri and H. Yamamoto, J. Org. Chem., 1992, 57, 1951; (f) E. J. Corey, C. L. Cywin and T. D. Roper, Tetrahedron Lett., 1992, 33, 6907; (g) K. Maruoka, T. Itoh, T. Shirasaka and H. Yamamoto, J. Am. Chem. Soc., 1988, 110, 310.
13. See e.g. (a) G. E. Keck, X.-Y. Li and D. Krishanmurthy, J. Org. Chem., 1995, 60, 5998; (b) M. Quimpére and K. Jankowski, J. Chem. Soc., Chem. Commun., 1987, 676; (c) A. Togni, Organometallics, 1990, 9, 3106; (d) Y. Motoyama and K. Mikami, J. Chem. Soc., Chem. Commun., 1994, 1563; (e) Q. Gao, M. Muruyama, M. Mouri and H. Yamamoto, J. Org. Chem., 1992, 57, 1951; (f) E. J. Corey, C. L. Cywin and T. D. Roper, Tetrahedron Lett., 1992, 33, 6907; (g) K. Maruoka, T. Itoh, T. Shirasaka and H. Yamamoto, J. Am. Chem. Soc., 1988, 110, 310.
14. See e.g. (a) G. E. Keck, X.-Y. Li and D. Krishanmurthy, J. Org. Chem., 1995, 60, 5998; (b) M. Quimpére and K. Jankowski, J. Chem. Soc., Chem. Commun., 1987, 676; (c) A. Togni, Organometallics, 1990, 9, 3106; (d) Y. Motoyama and K. Mikami, J. Chem. Soc., Chem. Commun., 1994, 1563; (e) Q. Gao, M. Muruyama, M. Mouri and H. Yamamoto, J. Org. Chem., 1992, 57, 1951; (f) E. J. Corey, C. L. Cywin and T. D. Roper, Tetrahedron Lett., 1992, 33, 6907; (g) K. Maruoka, T. Itoh, T. Shirasaka and H. Yamamoto, J. Am. Chem. Soc., 1988, 110, 310.
15. See e.g. (a) G. E. Keck, X.-Y. Li and D. Krishanmurthy, J. Org. Chem., 1995, 60, 5998; (b) M. Quimpére and K. Jankowski, J. Chem. Soc., Chem. Commun., 1987, 676; (c) A. Togni, Organometallics, 1990, 9, 3106; (d) Y. Motoyama and K. Mikami, J. Chem. Soc., Chem. Commun., 1994, 1563; (e) Q. Gao, M. Muruyama, M. Mouri and H. Yamamoto, J. Org. Chem., 1992, 57, 1951; (f) E. J. Corey, C. L. Cywin and T. D. Roper, Tetrahedron Lett., 1992, 33, 6907; (g) K. Maruoka, T. Itoh, T. Shirasaka and H. Yamamoto, J. Am. Chem. Soc., 1988, 110, 310.
16. See e.g. (a) G. E. Keck, X.-Y. Li and D. Krishanmurthy, J. Org. Chem., 1995, 60, 5998; (b) M. Quimpére and K. Jankowski, J. Chem. Soc., Chem. Commun., 1987, 676; (c) A. Togni, Organometallics, 1990, 9, 3106; (d) Y. Motoyama and K. Mikami, J. Chem. Soc., Chem. Commun., 1994, 1563; (e) Q. Gao, M. Muruyama, M. Mouri and H. Yamamoto, J. Org. Chem., 1992, 57, 1951; (f) E. J. Corey, C. L. Cywin and T. D. Roper, Tetrahedron Lett., 1992, 33, 6907; (g) K. Maruoka, T. Itoh, T. Shirasaka and H. Yamamoto, J. Am. Chem. Soc., 1988, 110, 310.
17. See e.g. (a) G. E. Keck, X.-Y. Li and D. Krishanmurthy, J. Org. Chem., 1995, 60, 5998; (b) M. Quimpére and K. Jankowski, J. Chem. Soc., Chem. Commun., 1987, 676; (c) A. Togni, Organometallics, 1990, 9, 3106; (d) Y. Motoyama and K. Mikami, J. Chem. Soc., Chem. Commun., 1994, 1563; (e) Q. Gao, M. Muruyama, M. Mouri and H. Yamamoto, J. Org. Chem., 1992, 57, 1951; (f) E. J. Corey, C. L. Cywin and T. D. Roper, Tetrahedron Lett., 1992, 33, 6907; (g) K. Maruoka, T. Itoh, T. Shirasaka and H. Yamamoto, J. Am. Chem. Soc., 1988, 110, 310.
18. K. Mikami, M. Terada and T. Nakai, J. Am. Chem. Soc., 1990, 112, 3949; K. Mikami, M. Terada and T. Nakai, J. Am. Chem. Soc, 1989, 111, 1940; K. Mikami, M. Terada, S. Narisawa and T. Nakai, Synlett, 1992, 255; M. Terada and K. Mikami, J. Chem. Soc., Chem. Commun., 1994, 833; M. Terada, S. Matsukawa and K. Mikami, J. Chem. Soc., Chem. Commun., 1993, 327.
19. K. Mikami, M. Terada and T. Nakai, J. Am. Chem. Soc., 1990, 112, 3949; K. Mikami, M. Terada and T. Nakai, J. Am. Chem. Soc, 1989, 111, 1940; K. Mikami, M. Terada, S. Narisawa and T. Nakai, Synlett, 1992, 255; M. Terada and K. Mikami, J. Chem. Soc., Chem. Commun., 1994, 833; M. Terada, S. Matsukawa and K. Mikami, J. Chem. Soc., Chem. Commun., 1993, 327.
20. K. Mikami, M. Terada and T. Nakai, J. Am. Chem. Soc., 1990, 112, 3949; K. Mikami, M. Terada and T. Nakai, J. Am. Chem. Soc, 1989, 111, 1940; K. Mikami, M. Terada, S. Narisawa and T. Nakai, Synlett, 1992, 255; M. Terada and K. Mikami, J. Chem. Soc., Chem. Commun., 1994, 833; M. Terada, S. Matsukawa and K. Mikami, J. Chem. Soc., Chem. Commun., 1993, 327.
21. K. Mikami, M. Terada and T. Nakai, J. Am. Chem. Soc., 1990, 112, 3949; K. Mikami, M. Terada and T. Nakai, J. Am. Chem. Soc, 1989, 111, 1940; K. Mikami, M. Terada, S. Narisawa and T. Nakai, Synlett, 1992, 255; M. Terada and K. Mikami, J. Chem. Soc., Chem. Commun., 1994, 833; M. Terada, S. Matsukawa and K. Mikami, J. Chem. Soc., Chem. Commun., 1993, 327.
22. K. Mikami, M. Terada and T. Nakai, J. Am. Chem. Soc., 1990, 112, 3949; K. Mikami, M. Terada and T. Nakai, J. Am. Chem. Soc, 1989, 111, 1940; K. Mikami, M. Terada, S. Narisawa and T. Nakai, Synlett, 1992, 255; M. Terada and K. Mikami, J. Chem. Soc., Chem. Commun., 1994, 833; M. Terada, S. Matsukawa and K. Mikami, J. Chem. Soc., Chem. Commun., 1993, 327.
23. For other BINOL-Al catalytic studies see e.g. (a) Y. Tamai, M. Someya, J. Fukumoto and S. Miyano, J. Chem. Soc., Chem. Commun., 1994, 1549; (b) H. Kouji and Y. Hayashi, Tetrahedron, 1993, 49, 1749; (c) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi and F. Sato, J. Org. Chem., 1995, 60, 3576; (d) M. Nishida, H. Hayashi, A. Nishida and N. Kawahara, Chem. Commun., 1996, 579; (e) M. Nishiuchi, K. Honda and T. Nakai, Chem. Lett., 1996, 321; (f) J. Bao, W. D. Wulff and A. L. Rheingold, J. Am. Chem. Soc., 1993, 115, 3814; (g) C. Chapuis and J. Jurczak, Helv. Chim. Acta, 1987, 77, 436; (h) A. Ketter, G. Glasl and R. Herrmann, J. Chem. Res. (S), 1990, 278; J. Chem. Res. (M), 1990, 2118; (i) T. Arai, H. Sasai, K.-i. Aoe, K. Okamura, T. Data and M. Shibasaki, Angew. Chem., 1996, 108, 103; (j) T. Arai, M. Bougauchi, H. Sasai and M. Shibasaki, J. Org. Chem., 1996, 61, 2926.
24. For other BINOL-Al catalytic studies see e.g. (a) Y. Tamai, M. Someya, J. Fukumoto and S. Miyano, J. Chem. Soc., Chem. Commun., 1994, 1549; (b) H. Kouji and Y. Hayashi, Tetrahedron, 1993, 49, 1749; (c) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi and F. Sato, J. Org. Chem., 1995, 60, 3576; (d) M. Nishida, H. Hayashi, A. Nishida and N. Kawahara, Chem. Commun., 1996, 579; (e) M. Nishiuchi, K. Honda and T. Nakai, Chem. Lett., 1996, 321; (f) J. Bao, W. D. Wulff and A. L. Rheingold, J. Am. Chem. Soc., 1993, 115, 3814; (g) C. Chapuis and J. Jurczak, Helv. Chim. Acta, 1987, 77, 436; (h) A. Ketter, G. Glasl and R. Herrmann, J. Chem. Res. (S), 1990, 278; J. Chem. Res. (M), 1990, 2118; (i) T. Arai, H. Sasai, K.-i. Aoe, K. Okamura, T. Data and M. Shibasaki, Angew. Chem., 1996, 108, 103; (j) T. Arai, M. Bougauchi, H. Sasai and M. Shibasaki, J. Org. Chem., 1996, 61, 2926.
25. For other BINOL-Al catalytic studies see e.g. (a) Y. Tamai, M. Someya, J. Fukumoto and S. Miyano, J. Chem. Soc., Chem. Commun., 1994, 1549; (b) H. Kouji and Y. Hayashi, Tetrahedron, 1993, 49, 1749; (c) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi and F. Sato, J. Org. Chem., 1995, 60, 3576; (d) M. Nishida, H. Hayashi, A. Nishida and N. Kawahara, Chem. Commun., 1996, 579; (e) M. Nishiuchi, K. Honda and T. Nakai, Chem. Lett., 1996, 321; (f) J. Bao, W. D. Wulff and A. L. Rheingold, J. Am. Chem. Soc., 1993, 115, 3814; (g) C. Chapuis and J. Jurczak, Helv. Chim. Acta, 1987, 77, 436; (h) A. Ketter, G. Glasl and R. Herrmann, J. Chem. Res. (S), 1990, 278; J. Chem. Res. (M), 1990, 2118; (i) T. Arai, H. Sasai, K.-i. Aoe, K. Okamura, T. Data and M. Shibasaki, Angew. Chem., 1996, 108, 103; (j) T. Arai, M. Bougauchi, H. Sasai and M. Shibasaki, J. Org. Chem., 1996, 61, 2926.
26. For other BINOL-Al catalytic studies see e.g. (a) Y. Tamai, M. Someya, J. Fukumoto and S. Miyano, J. Chem. Soc., Chem. Commun., 1994, 1549; (b) H. Kouji and Y. Hayashi, Tetrahedron, 1993, 49, 1749; (c) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi and F. Sato, J. Org. Chem., 1995, 60, 3576; (d) M. Nishida, H. Hayashi, A. Nishida and N. Kawahara, Chem. Commun., 1996, 579; (e) M. Nishiuchi, K. Honda and T. Nakai, Chem. Lett., 1996, 321; (f) J. Bao, W. D. Wulff and A. L. Rheingold, J. Am. Chem. Soc., 1993, 115, 3814; (g) C. Chapuis and J. Jurczak, Helv. Chim. Acta, 1987, 77, 436; (h) A. Ketter, G. Glasl and R. Herrmann, J. Chem. Res. (S), 1990, 278; J. Chem. Res. (M), 1990, 2118; (i) T. Arai, H. Sasai, K.-i. Aoe, K. Okamura, T. Data and M. Shibasaki, Angew. Chem., 1996, 108, 103; (j) T. Arai, M. Bougauchi, H. Sasai and M. Shibasaki, J. Org. Chem., 1996, 61, 2926.
27. For other BINOL-Al catalytic studies see e.g. (a) Y. Tamai, M. Someya, J. Fukumoto and S. Miyano, J. Chem. Soc., Chem. Commun., 1994, 1549; (b) H. Kouji and Y. Hayashi, Tetrahedron, 1993, 49, 1749; (c) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi and F. Sato, J. Org. Chem., 1995, 60, 3576; (d) M. Nishida, H. Hayashi, A. Nishida and N. Kawahara, Chem. Commun., 1996, 579; (e) M. Nishiuchi, K. Honda and T. Nakai, Chem. Lett., 1996, 321; (f) J. Bao, W. D. Wulff and A. L. Rheingold, J. Am. Chem. Soc., 1993, 115, 3814; (g) C. Chapuis and J. Jurczak, Helv. Chim. Acta, 1987, 77, 436; (h) A. Ketter, G. Glasl and R. Herrmann, J. Chem. Res. (S), 1990, 278; J. Chem. Res. (M), 1990, 2118; (i) T. Arai, H. Sasai, K.-i. Aoe, K. Okamura, T. Data and M. Shibasaki, Angew. Chem., 1996, 108, 103; (j) T. Arai, M. Bougauchi, H. Sasai and M. Shibasaki, J. Org. Chem., 1996, 61, 2926.
28. For other BINOL-Al catalytic studies see e.g. (a) Y. Tamai, M. Someya, J. Fukumoto and S. Miyano, J. Chem. Soc., Chem. Commun., 1994, 1549; (b) H. Kouji and Y. Hayashi, Tetrahedron, 1993, 49, 1749; (c) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi and F. Sato, J. Org. Chem., 1995, 60, 3576; (d) M. Nishida, H. Hayashi, A. Nishida and N. Kawahara, Chem. Commun., 1996, 579; (e) M. Nishiuchi, K. Honda and T. Nakai, Chem. Lett., 1996, 321; (f) J. Bao, W. D. Wulff and A. L. Rheingold, J. Am. Chem. Soc., 1993, 115, 3814; (g) C. Chapuis and J. Jurczak, Helv. Chim. Acta, 1987, 77, 436; (h) A. Ketter, G. Glasl and R. Herrmann, J. Chem. Res. (S), 1990, 278; J. Chem. Res. (M), 1990, 2118; (i) T. Arai, H. Sasai, K.-i. Aoe, K. Okamura, T. Data and M. Shibasaki, Angew. Chem., 1996, 108, 103; (j) T. Arai, M. Bougauchi, H. Sasai and M. Shibasaki, J. Org. Chem., 1996, 61, 2926.
29. For other BINOL-Al catalytic studies see e.g. (a) Y. Tamai, M. Someya, J. Fukumoto and S. Miyano, J. Chem. Soc., Chem. Commun., 1994, 1549; (b) H. Kouji and Y. Hayashi, Tetrahedron, 1993, 49, 1749; (c) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi and F. Sato, J. Org. Chem., 1995, 60, 3576; (d) M. Nishida, H. Hayashi, A. Nishida and N. Kawahara, Chem. Commun., 1996, 579; (e) M. Nishiuchi, K. Honda and T. Nakai, Chem. Lett., 1996, 321; (f) J. Bao, W. D. Wulff and A. L. Rheingold, J. Am. Chem. Soc., 1993, 115, 3814; (g) C. Chapuis and J. Jurczak, Helv. Chim. Acta, 1987, 77, 436; (h) A. Ketter, G. Glasl and R. Herrmann, J. Chem. Res. (S), 1990, 278; J. Chem. Res. (M), 1990, 2118; (i) T. Arai, H. Sasai, K.-i. Aoe, K. Okamura, T. Data and M. Shibasaki, Angew. Chem., 1996, 108, 103; (j) T. Arai, M. Bougauchi, H. Sasai and M. Shibasaki, J. Org. Chem., 1996, 61, 2926.
30. For other BINOL-Al catalytic studies see e.g. (a) Y. Tamai, M. Someya, J. Fukumoto and S. Miyano, J. Chem. Soc., Chem. Commun., 1994, 1549; (b) H. Kouji and Y. Hayashi, Tetrahedron, 1993, 49, 1749; (c) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi and F. Sato, J. Org. Chem., 1995, 60, 3576; (d) M. Nishida, H. Hayashi, A. Nishida and N. Kawahara, Chem. Commun., 1996, 579; (e) M. Nishiuchi, K. Honda and T. Nakai, Chem. Lett., 1996, 321; (f) J. Bao, W. D. Wulff and A. L. Rheingold, J. Am. Chem. Soc., 1993, 115, 3814; (g) C. Chapuis and J. Jurczak, Helv. Chim. Acta, 1987, 77, 436; (h) A. Ketter, G. Glasl and R. Herrmann, J. Chem. Res. (S), 1990, 278; J. Chem. Res. (M), 1990, 2118; (i) T. Arai, H. Sasai, K.-i. Aoe, K. Okamura, T. Data and M. Shibasaki, Angew. Chem., 1996, 108, 103; (j) T. Arai, M. Bougauchi, H. Sasai and M. Shibasaki, J. Org. Chem., 1996, 61, 2926.
31. For other BINOL-Al catalytic studies see e.g. (a) Y. Tamai, M. Someya, J. Fukumoto and S. Miyano, J. Chem. Soc., Chem. Commun., 1994, 1549; (b) H. Kouji and Y. Hayashi, Tetrahedron, 1993, 49, 1749; (c) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi and F. Sato, J. Org. Chem., 1995, 60, 3576; (d) M. Nishida, H. Hayashi, A. Nishida and N. Kawahara, Chem. Commun., 1996, 579; (e) M. Nishiuchi, K. Honda and T. Nakai, Chem. Lett., 1996, 321; (f) J. Bao, W. D. Wulff and A. L. Rheingold, J. Am. Chem. Soc., 1993, 115, 3814; (g) C. Chapuis and J. Jurczak, Helv. Chim. Acta, 1987, 77, 436; (h) A. Ketter, G. Glasl and R. Herrmann, J. Chem. Res. (S), 1990, 278; J. Chem. Res. (M), 1990, 2118; (i) T. Arai, H. Sasai, K.-i. Aoe, K. Okamura, T. Data and M. Shibasaki, Angew. Chem., 1996, 108, 103; (j) T. Arai, M. Bougauchi, H. Sasai and M. Shibasaki, J. Org. Chem., 1996, 61, 2926.
32. For other BINOL-Al catalytic studies see e.g. (a) Y. Tamai, M. Someya, J. Fukumoto and S. Miyano, J. Chem. Soc., Chem. Commun., 1994, 1549; (b) H. Kouji and Y. Hayashi, Tetrahedron, 1993, 49, 1749; (c) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi and F. Sato, J. Org. Chem., 1995, 60, 3576; (d) M. Nishida, H. Hayashi, A. Nishida and N. Kawahara, Chem. Commun., 1996, 579; (e) M. Nishiuchi, K. Honda and T. Nakai, Chem. Lett., 1996, 321; (f) J. Bao, W. D. Wulff and A. L. Rheingold, J. Am. Chem. Soc., 1993, 115, 3814; (g) C. Chapuis and J. Jurczak, Helv. Chim. Acta, 1987, 77, 436; (h) A. Ketter, G. Glasl and R. Herrmann, J. Chem. Res. (S), 1990, 278; J. Chem. Res. (M), 1990, 2118; (i) T. Arai, H. Sasai, K.-i. Aoe, K. Okamura, T. Data and M. Shibasaki, Angew. Chem., 1996, 108, 103; (j) T. Arai, M. Bougauchi, H. Sasai and M. Shibasaki, J. Org. Chem., 1996, 61, 2926.
33. For other BINOL-Al catalytic studies see e.g. (a) Y. Tamai, M. Someya, J. Fukumoto and S. Miyano, J. Chem. Soc., Chem. Commun., 1994, 1549; (b) H. Kouji and Y. Hayashi, Tetrahedron, 1993, 49, 1749; (c) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi and F. Sato, J. Org. Chem., 1995, 60, 3576; (d) M. Nishida, H. Hayashi, A. Nishida and N. Kawahara, Chem. Commun., 1996, 579; (e) M. Nishiuchi, K. Honda and T. Nakai, Chem. Lett., 1996, 321; (f) J. Bao, W. D. Wulff and A. L. Rheingold, J. Am. Chem. Soc., 1993, 115, 3814; (g) C. Chapuis and J. Jurczak, Helv. Chim. Acta, 1987, 77, 436; (h) A. Ketter, G. Glasl and R. Herrmann, J. Chem. Res. (S), 1990, 278; J. Chem. Res. (M), 1990, 2118; (i) T. Arai, H. Sasai, K.-i. Aoe, K. Okamura, T. Data and M. Shibasaki, Angew. Chem., 1996, 108, 103; (j) T. Arai, M. Bougauchi, H. Sasai and M. Shibasaki, J. Org. Chem., 1996, 61, 2926.
34. 4 reduction of the HDA product and comparison of the optical rotation with reported values: J. Jurczak and M. Tkacz, J. Org. Chem., 1979, 44, 3347.