Rh-catalyzed [4 + 2] carbocyclization of vinylarylaldehydes with alkenes and alkynes leading to substituted tetralones and 1-naphthols

Organic Letters

Volumn 9, Issue 11, 2007, Pages 2059-2062

  Tanaka, Ken ^a   Hojo, Daiki ^a   Shoji, Takeaki ^a   Hagiwara, Yuji ^a   Hirano, Masao ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34250629675     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0704587     Document Type: Article

References (34)

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29. Morehead and co-workers reported that this dimer formation can be decreased by decreasing the concentration of the aldehyde; see: Kundu, K.; McCullagh, J. V.; Morehead, A. T., Jr. J. Am. Chem. Soc. 2005, 127, 16042.
30. Electron-rich alkenes such as styrene, and substituted electron-deficient alkenes such as N,N-dimethylmethacrylamide and 1-pyrrolidinyl-2-buten-1- one failed to react with 4a.
31. The reaction of a substituted vinylbenzaldehyde such as 2-(1-phenylvinyl)benzaldehyde did not furnish the corresponding carbocyclization product.
32. 4-Methyl-2-alkylidenetetralone was generated as a major product (ca. 39% NMR yield), although this compound could not be isolated in pure form by silica gel chromatography.
33. Both electron-rich and electron-deficient internal alkynes such as 4-octyne and ethyl 2-butynoate failed to react with 4a. Synthesis of substituted phenols by [4 + 2] annulation of cyclobutenones with alkynes or alkenes, see: (a) Huffman, M. A.; Liebeskind, L. S. J. Am. Chem. Soc. 1991, 113, 2771.
34. (b) Kondo, T.; Niimi, M.; Nomura, M.; Wada, K.; Mitsudo, T. Tetrahedron Lett. 2007, 48, 2837.