Tandem Suzuki cross-coupling-Heck reactions

Tetrahedron Letters

Volumn 38, Issue 19, 1997, Pages 3455-3458

  Kojima, Akihiko ^a   Honzawa, Shinobu ^a   Boden, Christopher D J ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

NAPHTHALENE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030950718     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00644-8     Document Type: Article

References (27)

1. For a review of recent developments, see de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457 and references cited therein. For a comprehensive survey of synthetic organopalladium chemistry, see Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: New York, 1995.
2. For a review of recent developments, see de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457 and references cited therein. For a comprehensive survey of synthetic organopalladium chemistry, see Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: New York, 1995.
3. For a review of recent developments, see de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457 and references cited therein. For a comprehensive survey of synthetic organopalladium chemistry, see Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: New York, 1995.
4. For a review; see Grigg, R. J. Heterocycl. Chem. 1994, 31, 631. Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289.
5. For a review; see Grigg, R. J. Heterocycl. Chem. 1994, 31, 631. Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289.
6. (a) For asymmetric Heck reactions, see Shibasaki, M.; Sodeoka, M. J. Synth. Org. Chem. Jpn. 1994, 52, 956. Ashimori, A.; Matsuura, T.; Overman, L. E.; Poon, D. J. J. Org. Chem. 1993, 58, 6969. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845. Tietze, L. F.; Schimpf, R. Angew. Chem. Ed. Engl. 1994, 33, 1089. Sakuraba, S.; Awano, K.; Achiwa, K. Synlett 1994, 291. Moinet, C.; Fiaud, J.-C. Tetrahedron Lett. 1995, 36, 2051.
7. (a) For asymmetric Heck reactions, see Shibasaki, M.; Sodeoka, M. J. Synth. Org. Chem. Jpn. 1994, 52, 956. Ashimori, A.; Matsuura, T.; Overman, L. E.; Poon, D. J. J. Org. Chem. 1993, 58, 6969. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845. Tietze, L. F.; Schimpf, R. Angew. Chem. Ed. Engl. 1994, 33, 1089. Sakuraba, S.; Awano, K.; Achiwa, K. Synlett 1994, 291. Moinet, C.; Fiaud, J.-C. Tetrahedron Lett. 1995, 36, 2051.
8. (a) For asymmetric Heck reactions, see Shibasaki, M.; Sodeoka, M. J. Synth. Org. Chem. Jpn. 1994, 52, 956. Ashimori, A.; Matsuura, T.; Overman, L. E.; Poon, D. J. J. Org. Chem. 1993, 58, 6969. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845. Tietze, L. F.; Schimpf, R. Angew. Chem. Ed. Engl. 1994, 33, 1089. Sakuraba, S.; Awano, K.; Achiwa, K. Synlett 1994, 291. Moinet, C.; Fiaud, J.-C. Tetrahedron Lett. 1995, 36, 2051.
9. (a) For asymmetric Heck reactions, see Shibasaki, M.; Sodeoka, M. J. Synth. Org. Chem. Jpn. 1994, 52, 956. Ashimori, A.; Matsuura, T.; Overman, L. E.; Poon, D. J. J. Org. Chem. 1993, 58, 6969. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845. Tietze, L. F.; Schimpf, R. Angew. Chem. Ed. Engl. 1994, 33, 1089. Sakuraba, S.; Awano, K.; Achiwa, K. Synlett 1994, 291. Moinet, C.; Fiaud, J.-C. Tetrahedron Lett. 1995, 36, 2051.
10. (a) For asymmetric Heck reactions, see Shibasaki, M.; Sodeoka, M. J. Synth. Org. Chem. Jpn. 1994, 52, 956. Ashimori, A.; Matsuura, T.; Overman, L. E.; Poon, D. J. J. Org. Chem. 1993, 58, 6969. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845. Tietze, L. F.; Schimpf, R. Angew. Chem. Ed. Engl. 1994, 33, 1089. Sakuraba, S.; Awano, K.; Achiwa, K. Synlett 1994, 291. Moinet, C.; Fiaud, J.-C. Tetrahedron Lett. 1995, 36, 2051.
11. (a) For asymmetric Heck reactions, see Shibasaki, M.; Sodeoka, M. J. Synth. Org. Chem. Jpn. 1994, 52, 956. Ashimori, A.; Matsuura, T.; Overman, L. E.; Poon, D. J. J. Org. Chem. 1993, 58, 6969. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845. Tietze, L. F.; Schimpf, R. Angew. Chem. Ed. Engl. 1994, 33, 1089. Sakuraba, S.; Awano, K.; Achiwa, K. Synlett 1994, 291. Moinet, C.; Fiaud, J.-C. Tetrahedron Lett. 1995, 36, 2051.
12. (a) For asymmetric Heck reactions, see Shibasaki, M.; Sodeoka, M. J. Synth. Org. Chem. Jpn. 1994, 52, 956. Ashimori, A.; Matsuura, T.; Overman, L. E.; Poon, D. J. J. Org. Chem. 1993, 58, 6969. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845. Tietze, L. F.; Schimpf, R. Angew. Chem. Ed. Engl. 1994, 33, 1089. Sakuraba, S.; Awano, K.; Achiwa, K. Synlett 1994, 291. Moinet, C.; Fiaud, J.-C. Tetrahedron Lett. 1995, 36, 2051.
13. (b) For other interesting asymmetric reactions using palladium complexes, see Hosokawa, T.; Okuda, C.; Murahashi, S.-I. J. Org. Chem. 1985, 50, 1282 and references cited therein. Hayashi, T.; Niizuma, S.; Kamikawa, T.; Suzuki, N.; Uozumi, Y. J. Am. Chem. Soc. 1995, 117, 9101. For a review of allylic alkylations, see Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395.
14. (b) For other interesting asymmetric reactions using palladium complexes, see Hosokawa, T.; Okuda, C.; Murahashi, S.-I. J. Org. Chem. 1985, 50, 1282 and references cited therein. Hayashi, T.; Niizuma, S.; Kamikawa, T.; Suzuki, N.; Uozumi, Y. J. Am. Chem. Soc. 1995, 117, 9101. For a review of allylic alkylations, see Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395.
15. (b) For other interesting asymmetric reactions using palladium complexes, see Hosokawa, T.; Okuda, C.; Murahashi, S.-I. J. Org. Chem. 1985, 50, 1282 and references cited therein. Hayashi, T.; Niizuma, S.; Kamikawa, T.; Suzuki, N.; Uozumi, Y. J. Am. Chem. Soc. 1995, 117, 9101. For a review of allylic alkylations, see Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395.
16. Kojima, A.; Takemoto, T.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1996, 61, 4876.
17. A palladium catalyzed one-pot process in which a carbonylation reaction was carried out prior to a Heck-type reaction was reported. See Tour, J. M.; Negishi, E.-I. J. Am. Chem. Soc. 1985, 107, 8289. Suzuki, T.; Uozumi, Y.; Shibasaki, M. J. Chem. Soc., Chem. Commun. 1991, 1593. Grigg, R.; Putnikovic, B.; Urch, C. J. Tetrahedron Lett. 1996, 37, 695.
18. A palladium catalyzed one-pot process in which a carbonylation reaction was carried out prior to a Heck-type reaction was reported. See Tour, J. M.; Negishi, E.-I. J. Am. Chem. Soc. 1985, 107, 8289. Suzuki, T.; Uozumi, Y.; Shibasaki, M. J. Chem. Soc., Chem. Commun. 1991, 1593. Grigg, R.; Putnikovic, B.; Urch, C. J. Tetrahedron Lett. 1996, 37, 695.
19. A palladium catalyzed one-pot process in which a carbonylation reaction was carried out prior to a Heck-type reaction was reported. See Tour, J. M.; Negishi, E.-I. J. Am. Chem. Soc. 1985, 107, 8289. Suzuki, T.; Uozumi, Y.; Shibasaki, M. J. Chem. Soc., Chem. Commun. 1991, 1593. Grigg, R.; Putnikovic, B.; Urch, C. J. Tetrahedron Lett. 1996, 37, 695.
20. Farina, V. Pure Appl. Chem. 1996, 68, 73 and references cited therein.
21. Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844. Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. ibid. 1995, 34, 1848.
22. Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844. Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. ibid. 1995, 34, 1848.
23. Compounds 7 and 8 were prepared from known ia and ib. Kabbara, J.; Hoffmann, C.; Schinzer, D. Synthesis 1995, 299. equation presented
24. A useful intramolecular asymmetric Heck reaction using allylsilanes has been reported. See Tietze, L, F.; Raschke, T. Liebigs Ann. Chem. 1996, 1981 and references cited therein.
25. Compound 11 was prepared from the known ii as follows, and the relative configuration of 11 was determined by examination of NOEs in the nmr spectra of iva and ivb, derived from iii. See Caselli, A. S.; Collins, D. J.; Stone, G. M. Aust. J. Chem. 1982 35, 799. equation presented
26. The relative configuration of 13 was determined from the conversion of 13 to lactone v as follows. equation presented
27. 1H-NMR).