Rhodium(I)-catalyzed acylation of alkyne with acylsilane: Transformation of 5- or 6-alkynoylsilane to α-alkylidenecycloalkanone

Chemistry Letters

Volumn , Issue 12, 2001, Pages 1210-1211

  Yamane, Motoki ^a   Amemiya, Takuma ^a   Narasaka, Koichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035528499     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.1210     Document Type: Article

References (32)

1. H. Sakurai, M. Yamane, M. Iwata, N. Saito, and K. Narasaka, Chem. Lett., 1996, 841.
2. "Activation of Unreactive Bonds and Organic Synthesis," ed. by S. Murai. Springer, New York (1999); C.-H. Jun, D.-Y. Lee, H. Lee, and J.-B. Hong, Angew. Chem. Int. Ed., 39, 3070 (2000).
3. "Activation of Unreactive Bonds and Organic Synthesis," ed. by S. Murai. Springer, New York (1999); C.-H. Jun, D.-Y. Lee, H. Lee, and J.-B. Hong, Angew. Chem. Int. Ed., 39, 3070 (2000).
4. C.-H. Jun, D.-Y. Lee, Y.-H. Kim, and H. Lee, Organometallics, 20, 2928 (2001); C.-H. Jun, H. Lee, and S.-G. Lim, J. Am. Chem. Soc., 123, 751 (2001).
5. C.-H. Jun, D.-Y. Lee, Y.-H. Kim, and H. Lee, Organometallics, 20, 2928 (2001); C.-H. Jun, H. Lee, and S.-G. Lim, J. Am. Chem. Soc., 123, 751 (2001).
6. Very recently palladium(0)-catalyzed reaction of acylsilane with allylic ester was reported; Y. Obora, Y. Ogawa, Y. Imai, T. Kawamura, and Y. Tsuji, the 47th Symposium on Organometallic Chemistry, Japan, Nagoya, October, 2000, Abstr., No. B101.
7. For transition metal-catalyzed acylation reaction with acylstannane, see: E. Shirakawa, Y. Nakao, H. Yoshida, and T. Hiyama, J. Am. Chem. Soc., 122, 9030 (2000); E. Shirakawa, K. Yamasaki, H. Yoshida, and T. Hiyama, J. Am. Chem. Soc., 121, 10221 (1999).
8. For transition metal-catalyzed acylation reaction with acylstannane, see: E. Shirakawa, Y. Nakao, H. Yoshida, and T. Hiyama, J. Am. Chem. Soc., 122, 9030 (2000); E. Shirakawa, K. Yamasaki, H. Yoshida, and T. Hiyama, J. Am. Chem. Soc., 121, 10221 (1999).
9. A. R. Katritzky, H. Lang, Z. Wang, and Z. Lie, J. Org. Chem., 61, 7551 (1996). Acetic acid (80% in water) was used for the last hydrolysis step instead of 5 M HCl.
10. Cyclic vinyl ether was considered to be formed by the isomerization of alkyne to diene as reported: D. Ma and X. Lu, Tetrahedron, 46, 6319 (1990). In fact, when acylsilane 13 was treated with a catalytic amount of palladium diacetate and bis(diphenylphosphino)butane, dienoylsilane 16 was obtained in quantitative yield (eq 3). (equation presented)
11. For the Rh(1)-catalyzed Pauson-Khand type reaction, see: T. Kobayashi, Y. Koga, and K. Narasaka, J. Organomet. Chem., 624, 73 (2001); N. Jeong, B. K. Sung, and Y. K. Choi, J. Am. Chem. Soc., 122, 6771 (2000). For the cobalt-catalyzed reactions, see: B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, and S. H. Hwang, J. Am. Chem. Soc., 116, 8793 (1994); J. W. Kim and Y. K. Chung, Synthesis, 1998, 142; T. Sugihara and M. Yamaguchi, J. Am. Chem. Soc., 120, 10782 (1998); D. B. Belanger and T. Livinghouse, Tetrahedron Lett., 39, 7641 (1998); M. Hayashi Y. Hashimoto, Y. Yamamoto, J. Usuki, and K. Saigo, Angew. Chem. Int. Ed., 39, 631 (2000); K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe, Tetrahedron Asymm., 11, 797 (2000); K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe, Tetrahedron Lett., 41, 891 (2000). For the iridium-catalyzed reactions, see: T. Shibata and K. Takagi, J. Am. Chem. Soc., 122, 9852 (2000).
12. For the Rh(1)-catalyzed Pauson-Khand type reaction, see: T. Kobayashi, Y. Koga, and K. Narasaka, J. Organomet. Chem., 624, 73 (2001); N. Jeong, B. K. Sung, and Y. K. Choi, J. Am. Chem. Soc., 122, 6771 (2000). For the cobalt-catalyzed reactions, see: B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, and S. H. Hwang, J. Am. Chem. Soc., 116, 8793 (1994); J. W. Kim and Y. K. Chung, Synthesis, 1998, 142; T. Sugihara and M. Yamaguchi, J. Am. Chem. Soc., 120, 10782 (1998); D. B. Belanger and T. Livinghouse, Tetrahedron Lett., 39, 7641 (1998); M. Hayashi Y. Hashimoto, Y. Yamamoto, J. Usuki, and K. Saigo, Angew. Chem. Int. Ed., 39, 631 (2000); K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe, Tetrahedron Asymm., 11, 797 (2000); K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe, Tetrahedron Lett., 41, 891 (2000). For the iridium-catalyzed reactions, see: T. Shibata and K. Takagi, J. Am. Chem. Soc., 122, 9852 (2000).
13. For the Rh(1)-catalyzed Pauson-Khand type reaction, see: T. Kobayashi, Y. Koga, and K. Narasaka, J. Organomet. Chem., 624, 73 (2001); N. Jeong, B. K. Sung, and Y. K. Choi, J. Am. Chem. Soc., 122, 6771 (2000). For the cobalt-catalyzed reactions, see: B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, and S. H. Hwang, J. Am. Chem. Soc., 116, 8793 (1994); J. W. Kim and Y. K. Chung, Synthesis, 1998, 142; T. Sugihara and M. Yamaguchi, J. Am. Chem. Soc., 120, 10782 (1998); D. B. Belanger and T. Livinghouse, Tetrahedron Lett., 39, 7641 (1998); M. Hayashi Y. Hashimoto, Y. Yamamoto, J. Usuki, and K. Saigo, Angew. Chem. Int. Ed., 39, 631 (2000); K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe, Tetrahedron Asymm., 11, 797 (2000); K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe, Tetrahedron Lett., 41, 891 (2000). For the iridium-catalyzed reactions, see: T. Shibata and K. Takagi, J. Am. Chem. Soc., 122, 9852 (2000).
14. For the Rh(1)-catalyzed Pauson-Khand type reaction, see: T. Kobayashi, Y. Koga, and K. Narasaka, J. Organomet. Chem., 624, 73 (2001); N. Jeong, B. K. Sung, and Y. K. Choi, J. Am. Chem. Soc., 122, 6771 (2000). For the cobalt-catalyzed reactions, see: B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, and S. H. Hwang, J. Am. Chem. Soc., 116, 8793 (1994); J. W. Kim and Y. K. Chung, Synthesis, 1998, 142; T. Sugihara and M. Yamaguchi, J. Am. Chem. Soc., 120, 10782 (1998); D. B. Belanger and T. Livinghouse, Tetrahedron Lett., 39, 7641 (1998); M. Hayashi Y. Hashimoto, Y. Yamamoto, J. Usuki, and K. Saigo, Angew. Chem. Int. Ed., 39, 631 (2000); K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe, Tetrahedron Asymm., 11, 797 (2000); K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe, Tetrahedron Lett., 41, 891 (2000). For the iridium-catalyzed reactions, see: T. Shibata and K. Takagi, J. Am. Chem. Soc., 122, 9852 (2000).
15. For the Rh(1)-catalyzed Pauson-Khand type reaction, see: T. Kobayashi, Y. Koga, and K. Narasaka, J. Organomet. Chem., 624, 73 (2001); N. Jeong, B. K. Sung, and Y. K. Choi, J. Am. Chem. Soc., 122, 6771 (2000). For the cobalt-catalyzed reactions, see: B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, and S. H. Hwang, J. Am. Chem. Soc., 116, 8793 (1994); J. W. Kim and Y. K. Chung, Synthesis, 1998, 142; T. Sugihara and M. Yamaguchi, J. Am. Chem. Soc., 120, 10782 (1998); D. B. Belanger and T. Livinghouse, Tetrahedron Lett., 39, 7641 (1998); M. Hayashi Y. Hashimoto, Y. Yamamoto, J. Usuki, and K. Saigo, Angew. Chem. Int. Ed., 39, 631 (2000); K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe, Tetrahedron Asymm., 11, 797 (2000); K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe, Tetrahedron Lett., 41, 891 (2000). For the iridium-catalyzed reactions, see: T. Shibata and K. Takagi, J. Am. Chem. Soc., 122, 9852 (2000).
16. For the Rh(1)-catalyzed Pauson-Khand type reaction, see: T. Kobayashi, Y. Koga, and K. Narasaka, J. Organomet. Chem., 624, 73 (2001); N. Jeong, B. K. Sung, and Y. K. Choi, J. Am. Chem. Soc., 122, 6771 (2000). For the cobalt-catalyzed reactions, see: B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, and S. H. Hwang, J. Am. Chem. Soc., 116, 8793 (1994); J. W. Kim and Y. K. Chung, Synthesis, 1998, 142; T. Sugihara and M. Yamaguchi, J. Am. Chem. Soc., 120, 10782 (1998); D. B. Belanger and T. Livinghouse, Tetrahedron Lett., 39, 7641 (1998); M. Hayashi Y. Hashimoto, Y. Yamamoto, J. Usuki, and K. Saigo, Angew. Chem. Int. Ed., 39, 631 (2000); K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe, Tetrahedron Asymm., 11, 797 (2000); K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe, Tetrahedron Lett., 41, 891 (2000). For the iridium-catalyzed reactions, see: T. Shibata and K. Takagi, J. Am. Chem. Soc., 122, 9852 (2000).
17. For the Rh(1)-catalyzed Pauson-Khand type reaction, see: T. Kobayashi, Y. Koga, and K. Narasaka, J. Organomet. Chem., 624, 73 (2001); N. Jeong, B. K. Sung, and Y. K. Choi, J. Am. Chem. Soc., 122, 6771 (2000). For the cobalt-catalyzed reactions, see: B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, and S. H. Hwang, J. Am. Chem. Soc., 116, 8793 (1994); J. W. Kim and Y. K. Chung, Synthesis, 1998, 142; T. Sugihara and M. Yamaguchi, J. Am. Chem. Soc., 120, 10782 (1998); D. B. Belanger and T. Livinghouse, Tetrahedron Lett., 39, 7641 (1998); M. Hayashi Y. Hashimoto, Y. Yamamoto, J. Usuki, and K. Saigo, Angew. Chem. Int. Ed., 39, 631 (2000); K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe, Tetrahedron Asymm., 11, 797 (2000); K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe, Tetrahedron Lett., 41, 891 (2000). For the iridium-catalyzed reactions, see: T. Shibata and K. Takagi, J. Am. Chem. Soc., 122, 9852 (2000).
18. For the Rh(1)-catalyzed Pauson-Khand type reaction, see: T. Kobayashi, Y. Koga, and K. Narasaka, J. Organomet. Chem., 624, 73 (2001); N. Jeong, B. K. Sung, and Y. K. Choi, J. Am. Chem. Soc., 122, 6771 (2000). For the cobalt-catalyzed reactions, see: B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, and S. H. Hwang, J. Am. Chem. Soc., 116, 8793 (1994); J. W. Kim and Y. K. Chung, Synthesis, 1998, 142; T. Sugihara and M. Yamaguchi, J. Am. Chem. Soc., 120, 10782 (1998); D. B. Belanger and T. Livinghouse, Tetrahedron Lett., 39, 7641 (1998); M. Hayashi Y. Hashimoto, Y. Yamamoto, J. Usuki, and K. Saigo, Angew. Chem. Int. Ed., 39, 631 (2000); K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe, Tetrahedron Asymm., 11, 797 (2000); K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe, Tetrahedron Lett., 41, 891 (2000). For the iridium-catalyzed reactions, see: T. Shibata and K. Takagi, J. Am. Chem. Soc., 122, 9852 (2000).
19. For the Rh(1)-catalyzed Pauson-Khand type reaction, see: T. Kobayashi, Y. Koga, and K. Narasaka, J. Organomet. Chem., 624, 73 (2001); N. Jeong, B. K. Sung, and Y. K. Choi, J. Am. Chem. Soc., 122, 6771 (2000). For the cobalt-catalyzed reactions, see: B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, and S. H. Hwang, J. Am. Chem. Soc., 116, 8793 (1994); J. W. Kim and Y. K. Chung, Synthesis, 1998, 142; T. Sugihara and M. Yamaguchi, J. Am. Chem. Soc., 120, 10782 (1998); D. B. Belanger and T. Livinghouse, Tetrahedron Lett., 39, 7641 (1998); M. Hayashi Y. Hashimoto, Y. Yamamoto, J. Usuki, and K. Saigo, Angew. Chem. Int. Ed., 39, 631 (2000); K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe, Tetrahedron Asymm., 11, 797 (2000); K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe, Tetrahedron Lett., 41, 891 (2000). For the iridium-catalyzed reactions, see: T. Shibata and K. Takagi, J. Am. Chem. Soc., 122, 9852 (2000).
20. For the Rh(1)-catalyzed Pauson-Khand type reaction, see: T. Kobayashi, Y. Koga, and K. Narasaka, J. Organomet. Chem., 624, 73 (2001); N. Jeong, B. K. Sung, and Y. K. Choi, J. Am. Chem. Soc., 122, 6771 (2000). For the cobalt-catalyzed reactions, see: B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, and S. H. Hwang, J. Am. Chem. Soc., 116, 8793 (1994); J. W. Kim and Y. K. Chung, Synthesis, 1998, 142; T. Sugihara and M. Yamaguchi, J. Am. Chem. Soc., 120, 10782 (1998); D. B. Belanger and T. Livinghouse, Tetrahedron Lett., 39, 7641 (1998); M. Hayashi Y. Hashimoto, Y. Yamamoto, J. Usuki, and K. Saigo, Angew. Chem. Int. Ed., 39, 631 (2000); K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe, Tetrahedron Asymm., 11, 797 (2000); K. Hiroi, T. Watanabe, R. Kawagishi, and I. Abe, Tetrahedron Lett., 41, 891 (2000). For the iridium-catalyzed reactions, see: T. Shibata and K. Takagi, J. Am. Chem. Soc., 122, 9852 (2000).
21. For the examples of transmetallation between acylmetals and transitionmetals, see: L. S. Hegedus and R. Tamura, Organometallics, 1, 1188 (1982); T. Koga, S. Makinouchi, and N. Okukado, Chem. Lett., 1988, 1141; J.-B. Verlhac, E. Chanson, B. Jousseaume, and J.-P. Quintard, Tetrahedron Lett., 26, 6075 (1985); Y. Hanzawa, N. Tabuchi, and T. Taguchi, Tetrahedron Lett., 39, 6249 (1998); Y. Hanzawa, N. Tabuchi, K. Saito, S. Noguchi, and T. Taguchi, Angew. Chem. Int. Ed., 38, 2395 (1999); M. Yamane, Y. Ishibashi, H. Sakurai, and K. Narasaka, Chem. Lett., 2000, 174; H. Sakurai, K. Tanabe, and K. Narasaka, Chem. Lett., 2000, 168.
22. For the examples of transmetallation between acylmetals and transitionmetals, see: L. S. Hegedus and R. Tamura, Organometallics, 1, 1188 (1982); T. Koga, S. Makinouchi, and N. Okukado, Chem. Lett., 1988, 1141; J.-B. Verlhac, E. Chanson, B. Jousseaume, and J.-P. Quintard, Tetrahedron Lett., 26, 6075 (1985); Y. Hanzawa, N. Tabuchi, and T. Taguchi, Tetrahedron Lett., 39, 6249 (1998); Y. Hanzawa, N. Tabuchi, K. Saito, S. Noguchi, and T. Taguchi, Angew. Chem. Int. Ed., 38, 2395 (1999); M. Yamane, Y. Ishibashi, H. Sakurai, and K. Narasaka, Chem. Lett., 2000, 174; H. Sakurai, K. Tanabe, and K. Narasaka, Chem. Lett., 2000, 168.
23. For the examples of transmetallation between acylmetals and transitionmetals, see: L. S. Hegedus and R. Tamura, Organometallics, 1, 1188 (1982); T. Koga, S. Makinouchi, and N. Okukado, Chem. Lett., 1988, 1141; J.-B. Verlhac, E. Chanson, B. Jousseaume, and J.-P. Quintard, Tetrahedron Lett., 26, 6075 (1985); Y. Hanzawa, N. Tabuchi, and T. Taguchi, Tetrahedron Lett., 39, 6249 (1998); Y. Hanzawa, N. Tabuchi, K. Saito, S. Noguchi, and T. Taguchi, Angew. Chem. Int. Ed., 38, 2395 (1999); M. Yamane, Y. Ishibashi, H. Sakurai, and K. Narasaka, Chem. Lett., 2000, 174; H. Sakurai, K. Tanabe, and K. Narasaka, Chem. Lett., 2000, 168.
24. For the examples of transmetallation between acylmetals and transitionmetals, see: L. S. Hegedus and R. Tamura, Organometallics, 1, 1188 (1982); T. Koga, S. Makinouchi, and N. Okukado, Chem. Lett., 1988, 1141; J.-B. Verlhac, E. Chanson, B. Jousseaume, and J.-P. Quintard, Tetrahedron Lett., 26, 6075 (1985); Y. Hanzawa, N. Tabuchi, and T. Taguchi, Tetrahedron Lett., 39, 6249 (1998); Y. Hanzawa, N. Tabuchi, K. Saito, S. Noguchi, and T. Taguchi, Angew. Chem. Int. Ed., 38, 2395 (1999); M. Yamane, Y. Ishibashi, H. Sakurai, and K. Narasaka, Chem. Lett., 2000, 174; H. Sakurai, K. Tanabe, and K. Narasaka, Chem. Lett., 2000, 168.
25. For the examples of transmetallation between acylmetals and transitionmetals, see: L. S. Hegedus and R. Tamura, Organometallics, 1, 1188 (1982); T. Koga, S. Makinouchi, and N. Okukado, Chem. Lett., 1988, 1141; J.-B. Verlhac, E. Chanson, B. Jousseaume, and J.-P. Quintard, Tetrahedron Lett., 26, 6075 (1985); Y. Hanzawa, N. Tabuchi, and T. Taguchi, Tetrahedron Lett., 39, 6249 (1998); Y. Hanzawa, N. Tabuchi, K. Saito, S. Noguchi, and T. Taguchi, Angew. Chem. Int. Ed., 38, 2395 (1999); M. Yamane, Y. Ishibashi, H. Sakurai, and K. Narasaka, Chem. Lett., 2000, 174; H. Sakurai, K. Tanabe, and K. Narasaka, Chem. Lett., 2000, 168.
26. For the examples of transmetallation between acylmetals and transitionmetals, see: L. S. Hegedus and R. Tamura, Organometallics, 1, 1188 (1982); T. Koga, S. Makinouchi, and N. Okukado, Chem. Lett., 1988, 1141; J.-B. Verlhac, E. Chanson, B. Jousseaume, and J.-P. Quintard, Tetrahedron Lett., 26, 6075 (1985); Y. Hanzawa, N. Tabuchi, and T. Taguchi, Tetrahedron Lett., 39, 6249 (1998); Y. Hanzawa, N. Tabuchi, K. Saito, S. Noguchi, and T. Taguchi, Angew. Chem. Int. Ed., 38, 2395 (1999); M. Yamane, Y. Ishibashi, H. Sakurai, and K. Narasaka, Chem. Lett., 2000, 174; H. Sakurai, K. Tanabe, and K. Narasaka, Chem. Lett., 2000, 168.
27. For the examples of transmetallation between acylmetals and transitionmetals, see: L. S. Hegedus and R. Tamura, Organometallics, 1, 1188 (1982); T. Koga, S. Makinouchi, and N. Okukado, Chem. Lett., 1988, 1141; J.-B. Verlhac, E. Chanson, B. Jousseaume, and J.-P. Quintard, Tetrahedron Lett., 26, 6075 (1985); Y. Hanzawa, N. Tabuchi, and T. Taguchi, Tetrahedron Lett., 39, 6249 (1998); Y. Hanzawa, N. Tabuchi, K. Saito, S. Noguchi, and T. Taguchi, Angew. Chem. Int. Ed., 38, 2395 (1999); M. Yamane, Y. Ishibashi, H. Sakurai, and K. Narasaka, Chem. Lett., 2000, 174; H. Sakurai, K. Tanabe, and K. Narasaka, Chem. Lett., 2000, 168.
28. For acid-catalyzed reaction of aldehyde with alkyne, see: A. Hayashi, M. Yamaguchi, and M. Hirama, Synlett, 1995, 195.
29. For transition metal-catalyzed hydro-acylation of alkyne, see: K. Kokubo, K. Matsumasa, Y. Nishinaka, M. Miura, and M. Nomura, Bull. Chem. Soc. Jpn., 72, 303 (1999); K. Kokubo, K. Matsumasa, M. Miura, and M. Nomura, J. Org. Chem., 62, 4564 (1997); H. Lee and C.-H. Jun, Bull. Korean Chem. Soc., 16, 1135 (1995); T. Tsuda, T. Kiyoi, and T. Saegusa, J. Org. Chem., 55, 2554 (1990).
30. For transition metal-catalyzed hydro-acylation of alkyne, see: K. Kokubo, K. Matsumasa, Y. Nishinaka, M. Miura, and M. Nomura, Bull. Chem. Soc. Jpn., 72, 303 (1999); K. Kokubo, K. Matsumasa, M. Miura, and M. Nomura, J. Org. Chem., 62, 4564 (1997); H. Lee and C.-H. Jun, Bull. Korean Chem. Soc., 16, 1135 (1995); T. Tsuda, T. Kiyoi, and T. Saegusa, J. Org. Chem., 55, 2554 (1990).
31. For transition metal-catalyzed hydro-acylation of alkyne, see: K. Kokubo, K. Matsumasa, Y. Nishinaka, M. Miura, and M. Nomura, Bull. Chem. Soc. Jpn., 72, 303 (1999); K. Kokubo, K. Matsumasa, M. Miura, and M. Nomura, J. Org. Chem., 62, 4564 (1997); H. Lee and C.-H. Jun, Bull. Korean Chem. Soc., 16, 1135 (1995); T. Tsuda, T. Kiyoi, and T. Saegusa, J. Org. Chem., 55, 2554 (1990).
32. For transition metal-catalyzed hydro-acylation of alkyne, see: K. Kokubo, K. Matsumasa, Y. Nishinaka, M. Miura, and M. Nomura, Bull. Chem. Soc. Jpn., 72, 303 (1999); K. Kokubo, K. Matsumasa, M. Miura, and M. Nomura, J. Org. Chem., 62, 4564 (1997); H. Lee and C.-H. Jun, Bull. Korean Chem. Soc., 16, 1135 (1995); T. Tsuda, T. Kiyoi, and T. Saegusa, J. Org. Chem., 55, 2554 (1990).