Diastereoselective Formation of Indanes from Arylboronate Esters Catalyzed by Rhodium(I) in Aqueous Media

Organic Letters

Volumn 4, Issue 12, 2002, Pages 2105-2108

  Lautens, Mark ^a   Mancuso, John ^a  

^a UNIVERSITY OF TORONTO   (Canada)

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[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0013246404     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0260627     Document Type: Article

References (25)

1. (1)(a) Cornils, B.; Herrmann, W. A. Aqueous-Phase Organometallic Catalysis; Wiley-VCH: Weinheim, Germany, 1998.
2. (b) Horváth, I. T.; Joó, F. Aqueous Organometallic Chemistry and Catalysis; Kluwer Academic: Dordrecht, The Netherlands, 1995.
3. (c) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; Wiley-Interscience: New York, 1997.
4. Selected recent references: (a) Murakami, M.; Igawa, H. Chem. Commun. 2002, 4, 390. (b) Lautens, M.; Yoshida, M. Org. Lett. 2002, 4, 123. (c) Frost, C. G.; Wadsworth, K. J. Chem. Commun. 2001, 22, 2316. Asymmetric additions: (d) Hayashi, T. Synlett 2001, Spec. Iss., 879. (e) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (f) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 7, 722.
5. Selected recent references: (a) Murakami, M.; Igawa, H. Chem. Commun. 2002, 4, 390. (b) Lautens, M.; Yoshida, M. Org. Lett. 2002, 4, 123. (c) Frost, C. G.; Wadsworth, K. J. Chem. Commun. 2001, 22, 2316. Asymmetric additions: (d) Hayashi, T. Synlett 2001, Spec. Iss., 879. (e) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (f) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 7, 722.
6. Selected recent references: (a) Murakami, M.; Igawa, H. Chem. Commun. 2002, 4, 390. (b) Lautens, M.; Yoshida, M. Org. Lett. 2002, 4, 123. (c) Frost, C. G.; Wadsworth, K. J. Chem. Commun. 2001, 22, 2316. Asymmetric additions: (d) Hayashi, T. Synlett 2001, Spec. Iss., 879. (e) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (f) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 7, 722.
7. Selected recent references: (a) Murakami, M.; Igawa, H. Chem. Commun. 2002, 4, 390. (b) Lautens, M.; Yoshida, M. Org. Lett. 2002, 4, 123. (c) Frost, C. G.; Wadsworth, K. J. Chem. Commun. 2001, 22, 2316. Asymmetric additions: (d) Hayashi, T. Synlett 2001, Spec. Iss., 879. (e) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (f) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 7, 722.
8. Selected recent references: (a) Murakami, M.; Igawa, H. Chem. Commun. 2002, 4, 390. (b) Lautens, M.; Yoshida, M. Org. Lett. 2002, 4, 123. (c) Frost, C. G.; Wadsworth, K. J. Chem. Commun. 2001, 22, 2316. Asymmetric additions: (d) Hayashi, T. Synlett 2001, Spec. Iss., 879. (e) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (f) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 7, 722.
9. Selected recent references: (a) Murakami, M.; Igawa, H. Chem. Commun. 2002, 4, 390. (b) Lautens, M.; Yoshida, M. Org. Lett. 2002, 4, 123. (c) Frost, C. G.; Wadsworth, K. J. Chem. Commun. 2001, 22, 2316. Asymmetric additions: (d) Hayashi, T. Synlett 2001, Spec. Iss., 879. (e) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944. (f) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 7, 722.
10. (a) Oi, S.; Honma, Y.; Inoue, Y. Org. Lett. 2002, 4, 667.
11. (b) Mori, A.; Danda, Y.; Fujii, T.; Hirabayashi, K.; Osakada, K. J. Am. Chem. Soc. 2001, 123, 10774.
12. (c) Huang, T. S.; Li, C.-J. Chem. Commun. 2001, 22, 2348.
13. (a) Huang, T.; Meng, Y.; Venkatraman, S.; Wang, D.; Li, C.-J. J. Am. Chem. Soc. 2001, 123, 7451.
14. (b) Oi, S.; Moro, M.; Ito, H.; Honma, Y.; Miyano, S.; Inoue, Y. Tetrahedron 2002, 58, 91.
15. (a) Larock, R. C.; Bernhardt, J. C. J. Org. Chem. 1977, 42, 180.
16. (b) Larock, R. C.; Hershberger, S. S. J. Org. Chem. 1980, 45, 3840.
17. Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martin-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358.
18. For selected reviews on Pd cascade reactions, see: (a) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289. (b) Grigg, R.; Sridharan, V. J. Organomet. Chem. 1999, 576, 65.
19. For selected reviews on Pd cascade reactions, see: (a) Heumann, A.; Réglier, M. Tetrahedron 1996, 52, 9289. (b) Grigg, R.; Sridharan, V. J. Organomet. Chem. 1999, 576, 65.
20. Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Organomet. Chem. 2002, 648, 297.
21. (a) For preparation of t-Bu-amphos Cl (2) and account of its efficiency for Pd-catalyzed Suzuki couplings in aqueous media, see: Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (b) Original amphos ligand: Smith, R. T.; Baird, M. C. Inorg. Chim. Acta 1982, 62, 135.
22. (a) For preparation of t-Bu-amphos Cl (2) and account of its efficiency for Pd-catalyzed Suzuki couplings in aqueous media, see: Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (b) Original amphos ligand: Smith, R. T.; Baird, M. C. Inorg. Chim. Acta 1982, 62, 135.
23. Trost, B. M. Science 1991, 254, 1471.
24. Uson, R.; Oro, L. A.; Cabeza, J. A. Inorg. Synth. 1985, 23, 126.
25. Stereochemistry of 6 proved by hydrogenation, which gives only product 4.