Ruthenium-catalyzed regioselective α-alkylation of ketones with primary alcohols

Tetrahedron Letters

Volumn 43, Issue 44, 2002, Pages 7987-7989

  Cho, Chan Sik ^a   Kim, Bok Tae ^a   Kim, Tae Jeong ^a   Chul Shim, Sang ^a  

^a Kyungpook National University   (South Korea)

Author keywords

Alkylation; Ketones; Primary alcohols; Ruthenium catalyst

Indexed keywords

ALCOHOL DERIVATIVE; ALKYL GROUP; HYDROGEN; KETONE DERIVATIVE; POTASSIUM HYDROXIDE; RUTHENIUM;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; TEMPERATURE;

EID: 0037190865     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01625-8     Document Type: Article

References (26)

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2. Transition metal-catalyzed direct α-alkylation of ketones: (a) Inoue, Y.; Toyofuku, M.; Taguchi, M.; Okada, S.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1986, 59, 885; (b) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168; (c) Camacho, D. H.; Nakamura, I.; Oh, B. H.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2002, 43, 2903.
3. Transition metal-catalyzed direct α-alkylation of ketones: (a) Inoue, Y.; Toyofuku, M.; Taguchi, M.; Okada, S.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1986, 59, 885; (b) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168; (c) Camacho, D. H.; Nakamura, I.; Oh, B. H.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2002, 43, 2903.
4. Transition metal-catalyzed direct α-alkylation of ketones: (a) Inoue, Y.; Toyofuku, M.; Taguchi, M.; Okada, S.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1986, 59, 885; (b) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168; (c) Camacho, D. H.; Nakamura, I.; Oh, B. H.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2002, 43, 2903.
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17. This methodology could also be successfully applied to modified Friedlaender quinoline synthesis by the ruthenium-catalyzed oxidative cyclization of 2-aminobenzyl alcohol with ketones: Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2001, 2576.
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23. A reviewer suggested that 1-dodecene is possible to work as a ligand and thus needs a catalytic amount. However, a separate experiment using a catalytic amount of 1-dodecene (10 mol%) gave similar results (3, 67%; 4, 16%) as that when the reaction was carried out in the absence of 1-dodecene.
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