Chelation-Assisted Hydroesterification of Alkenes Catalyzed by Rhodium Complex

Organic Letters

Volumn 5, Issue 23, 2003, Pages 4329-4331

  Yokota, Kazuhiko ^a   Tatamidani, Hiroto ^a   Fukumoto, Yoshiya ^a   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKENE DERIVATIVE; PYRIDINE DERIVATIVE; RHODIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHELATION; CHEMICAL REACTION; ESTERIFICATION;

EID: 0344496824     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035582e     Document Type: Article

References (19)

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7. For recent papers on chelation-assisted reactions, see: Jun, C.-H.; Moon, C. W.; Hong, J.-B.; Lim, S.-G.; Chung, K.-Y.; Kim, Y.-H. Chem. Eur. J. 2002, 485. Bendorf, H. D.; Colella, C. M.; Dixon, E. C.; Marchetti, M.; Matukonis, A. N.; Musselman, J. D.; Tiley, T. A. Tetrahedron Lett. 2002, 43, 7031. Itami, K.; Mitsudo, K.; Yoshida, J. Angew. Chem., Int. Ed. 2002, 41, 3481. Ko, S.; Han, H. ; Chang, S. Org. Lett. 2003, 5, 2687.
8. For recent papers on chelation-assisted reactions, see: Jun, C.-H.; Moon, C. W.; Hong, J.-B.; Lim, S.-G.; Chung, K.-Y.; Kim, Y.-H. Chem. Eur. J. 2002, 485. Bendorf, H. D.; Colella, C. M.; Dixon, E. C.; Marchetti, M.; Matukonis, A. N.; Musselman, J. D.; Tiley, T. A. Tetrahedron Lett. 2002, 43, 7031. Itami, K.; Mitsudo, K.; Yoshida, J. Angew. Chem., Int. Ed. 2002, 41, 3481. Ko, S.; Han, H. ; Chang, S. Org. Lett. 2003, 5, 2687.
9. For recent papers on chelation-assisted reactions, see: Jun, C.-H.; Moon, C. W.; Hong, J.-B.; Lim, S.-G.; Chung, K.-Y.; Kim, Y.-H. Chem. Eur. J. 2002, 485. Bendorf, H. D.; Colella, C. M.; Dixon, E. C.; Marchetti, M.; Matukonis, A. N.; Musselman, J. D.; Tiley, T. A. Tetrahedron Lett. 2002, 43, 7031. Itami, K.; Mitsudo, K.; Yoshida, J. Angew. Chem., Int. Ed. 2002, 41, 3481. Ko, S.; Han, H. ; Chang, S. Org. Lett. 2003, 5, 2687.
10. For our recent paper on a chelation-assisted carbonylation at C - H bonds, see: Asaumi, T.; Chatani, N.; Matsuo, T.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2003, 68, 7538.
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14. 12 (0.04 mmol) gave a trace amount of heptanoic acid benzyl ester. When pyridine (2 mmol) was added, the benzyl ester was formed in 13% yield (n:i = 92:8). The use of 4-pyridylmethanol gave the corresponding ester in 13% yield (n:i = 95:5).
15. 12, 2 was obtained in 35% yield (n:i = 82:18).
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19. 12 as the catalyst. No CO is required. Ko, S.; Na, Y.; Chang, S. J. Am. Chem. Soc. 2002, 124, 750.