Synthesis of contiguous cyclopropanes by palladium-catalyzed Suzuki-type cross-coupling reactions

Tetrahedron Letters

Volumn 38, Issue 16, 1997, Pages 2809-2812

  Charette, André B ^a   De Freitas Gil, Rossimiriam Pereira ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; REACTION ANALYSIS;

EID: 0342894707     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00478-4     Document Type: Article

References (19)

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2. For a review on the Suzuki reaction, see: Suzuki, A.; Miyaura, N. Chem. Rev. 1995, 95, 2457-2483.
3. Two Suzuki-type cross coupling reactions between cyclopropylboronic acids and aryl iodides and bromides have recently been reported: (a) Hildebrand, J. P.; Marsden, S. P. Synlett 1996, 893-894.
4. (b) Wang, X.-Z.; Deng, M.-Z. J. Chem. Soc. Perkin Trans I 1996, 2663-2664.
5. For a Negishi-type coupling of cyclopropylstannane, see: Piers, E.; Jean, M.; Marrs, P. S. Tetrahedron Lett. 1987, 28, 5075-5078.
6. (a) FR-900848: Yoshida, M.; Ezaki, M.; Hashimoto, M. Yamashita, M.; Shigematsu, N.; Okuhara, M.; Kohsaka, M.; Horikoshi, K. J. Antibiotics 1990, 43, 748-754.
7. (b) U-106305: Kuo, M. S.; Zielinski, R. J.; Cialdella, J. I.; Marschke, C. K.; Dupuis, M. J.; Li, G. P. ; Kloosterman, D. A.; Spilman, C. H.; Marshall, V. P. J. Am. Chem. Soc. 1995, 117, 10629-10634.
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9. (b) Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169-5171.
10. Larhed, M.; Lindeberg, G.; Hallberg, A. Tetrahedron Lett. 1996, 37, 8219-8222.
11. For symmetrical coupling of cyclopropanes, see: Falck, J. R.; Mekonnen, B.; Yu, J.; Lai, J.-Y. J. Am. Chem. Soc. 1996, 118, 6096-6097 and references cited therein.
12. (a) Fontani, P.; Carboni, B.; Vaultier, M.; Maas, G. Synthesis 1991, 605-609.
13. (b) Fontani, P.; Carboni, B.; Vaultier, M.; Carrié, R. Tetrahedron Lett. 1989, 30, 4815-4818.
14. 2/Pd(OAc)2 treatment. Ester 3 was prepared by mixing boronic acid 6 and catechol (pentane).
15. These compounds can also be prepared in enantiomerically enriched forms: Imai, T.; Mineta, H.; Nishida, S. J. Org. Chem. 1990, 55, 4986-4988.
16. (a) Brown, H. C.; Gupta, S. K. J. Am. Chem. Soc. 1972, 94, 4370-4371.
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18. Zhang, H.; Chan, K. S. Tetrahedron Lett. 1996, 37, 1043-1044.
19. 2O) of the corresponding diol used as the boronate ester increases: catechol: 9.48; ethylene glycol: 14.8-15.1, 1,3-propanediol: 15.1.