Double-chelation-assisted Rh-catalyzed intermolecular hydroacylation

Organic Letters

Volumn 5, Issue 8, 2003, Pages 1365-1367

  Tanaka, Masakazu ^a   Imai, Masanori ^b   Yamamoto, Yoichiro ^a   Tanaka, Keitaro ^a   Shimowatari, Masato ^a   Nagumo, Shinji ^b   Kawahara, Norio ^b   Suemune, Hiroshi ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b HOKKAIDO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; RHODIUM COMPLEX; SALICYLALDEHYDE;

ACYLATION; ARTICLE; CATALYSIS; CHELATION; MOLECULAR DYNAMICS;

EID: 0141740674     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034343o     Document Type: Article

References (32)

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24. Distance between the two olefins is too long for the chelation.
25. 6-ph-bi-Rh-complex or heptacoordinated Rh may exist in chelations of both salicylaldehyde and diene. See: Nagashima, H.; Tatebe, K.; Ishibashi, T.; Nakaoka, A.; Sakakibara, J.; Itoh, K. Organometallics 1995, 14, 2868. See also ref 1b.
26. 2 was completed in 15 min, and 10a,b were obtained in 90%.
27. Additives of bases and alcohols may affect the phenolic hydroxy group and change the chelation effects, and those of Ag salts may affect the property of the Rh complex.
28. Ratio of regioisomers was very sensitive to the reaction conditions.
29. 2 was observed by Jun. See ref 5a and: Jun, C.-H. J. Organomet. Chem. 1990, 390, 361. Also, for chelations of imine bearing picoline and allyl alcohol, see: Jun, C.-H.; Han, J.-S.; Kang, J.-B.; Kim, S. J. Organomet. Chem. 1994, 474, 183.
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32. 3, see ref 11.