Application of Rh(l)-Catalyzed C - H Bond Activation to the Ring Opening of 2-Cycloalkenones in the Presence of Amines

Organic Letters

Volumn 4, Issue 9, 2002, Pages 1595-1597

  Jun, Chul Ho ^a   Moon, Choong Woon ^a   Lim, Sung Gon ^a   Lee, Hyuk ^a  

^a Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038075536     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025816e     Document Type: Article

References (24)

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15. Jun, C.-H.; Lee, H.; Moon, C. W.; Hong, H.-S. J. Am. Chem. Soc. 2001, 123, 8600-8601. (5) 2-Cycloalkenones larger than 2-cycloheptenone were prepared by the known procedures as described in Supporting Information. See:
16. (a) Ito, Y.; Fujii, S.; Nakatsuka, M.; Kawamoto, F.; Saegusa, T. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, pp 327-333.
17. (a) Ito, Y.; Fujii, S.; Nakatsuka, M.; Kawamoto, F.; Saegusa, T. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, pp 327-333.
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19. For the C-C double bond cleavage of conjugated enones by amines, see: (a) Eisch, J. J.; Sanchez, R. J. Org. Chem. 1986, 51, 1848-1852.
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22. 2 under Pd/C; see Supporting Information. This result shows that 14b is not a good substrate for β-alkylation.
23. The Ru-catalyzed direct β-alkylation is only applicable to the vinyl silane or vinyl siloxane. For example, see: (a) Trost, B. M.; Imi, K.; Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371-5372.
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