Stereoselectivity control in the Rh(I)-catalyzed conjugate additions of aryl and alkenylboronic acids to unprotected hydroxycyclopentenones

Organic Letters

Volumn 7, Issue 8, 2005, Pages 1669-1671

  De La Herrán, Gabriela ^a   Mba, Miriam ^a   Murcia, M Carmen ^a   Plumet, Joaquín ^a   Csáky, Aurelio G ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUP; BORONIC ACID DERIVATIVE; CYCLOPENTENONE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RHODIUM DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CIS ISOMER; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TRANS ISOMER;

EID: 17844373774     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050462n     Document Type: Article

References (29)

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22. The fluoride anion promotes transmetalation from boron to Pd(II) species. This has been extensively used in Suzuki couplings. For recent reviews, see: (a) Miyaura, N. Top. Curr. Chem. 2002, 219, 11. (b) Suzuki, A. J. Organomet. Chem. 2002, 653, 83.
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25. From the crystal structures of arylrhodium(I) compounds it is known that the orientation of the aryl group is orthogonal to the square plane of the complex in order to minimize steric interactions with the remaining ligands on the metal. See ref 3a and: (a) Dahlenburg, L.; Yardimciolu, A.; Hock, N. Inorg. Chim. Acta 1984, 89, 213. (b) Hay-Motherwell, R. S.; Koscmieder, S. U.; Wilkinson, G.; Hussain-Bates, B.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1991, 2821. (c) Boyd, S. E.; Field, L. D.; Hambley, T. W.; Partridge, M. G. Organometallics 1993, 12, 1720. (d) Yamamoto, M.; Onitsuka, K.; Takahashi, S. Organometallics 2000, 19, 4669.
26. From the crystal structures of arylrhodium(I) compounds it is known that the orientation of the aryl group is orthogonal to the square plane of the complex in order to minimize steric interactions with the remaining ligands on the metal. See ref 3a and: (a) Dahlenburg, L.; Yardimciolu, A.; Hock, N. Inorg. Chim. Acta 1984, 89, 213. (b) Hay-Motherwell, R. S.; Koscmieder, S. U.; Wilkinson, G.; Hussain-Bates, B.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1991, 2821. (c) Boyd, S. E.; Field, L. D.; Hambley, T. W.; Partridge, M. G. Organometallics 1993, 12, 1720. (d) Yamamoto, M.; Onitsuka, K.; Takahashi, S. Organometallics 2000, 19, 4669.
27. From the crystal structures of arylrhodium(I) compounds it is known that the orientation of the aryl group is orthogonal to the square plane of the complex in order to minimize steric interactions with the remaining ligands on the metal. See ref 3a and: (a) Dahlenburg, L.; Yardimciolu, A.; Hock, N. Inorg. Chim. Acta 1984, 89, 213. (b) Hay-Motherwell, R. S.; Koscmieder, S. U.; Wilkinson, G.; Hussain-Bates, B.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1991, 2821. (c) Boyd, S. E.; Field, L. D.; Hambley, T. W.; Partridge, M. G. Organometallics 1993, 12, 1720. (d) Yamamoto, M.; Onitsuka, K.; Takahashi, S. Organometallics 2000, 19, 4669.
28. From the crystal structures of arylrhodium(I) compounds it is known that the orientation of the aryl group is orthogonal to the square plane of the complex in order to minimize steric interactions with the remaining ligands on the metal. See ref 3a and: (a) Dahlenburg, L.; Yardimciolu, A.; Hock, N. Inorg. Chim. Acta 1984, 89, 213. (b) Hay-Motherwell, R. S.; Koscmieder, S. U.; Wilkinson, G.; Hussain-Bates, B.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1991, 2821. (c) Boyd, S. E.; Field, L. D.; Hambley, T. W.; Partridge, M. G. Organometallics 1993, 12, 1720. (d) Yamamoto, M.; Onitsuka, K.; Takahashi, S. Organometallics 2000, 19, 4669.
29. Alternatively, the formation of a Rh(III) species may be invoked. See: Albrecht, M.; Crabtree, R. H.; Mata, J.; Peris, E. Chem. Commun. 2002, 32.