Advances in Cycloaddition. Volume 5 by M. Harmata

By M. Harmata

The advance and alertness of cycloaddition method remains to be on the leading edge of study in artificial natural chemistry. This quantity starts off with a evaluate of equipment on hand for the synthesis of 7-membered jewelry and is with paintings on metal-catalyzed cycloadditions. there's then an replace at the cycloaddition chemistry of 2-pyrone, after which a distinct program of photocycloaddition is unique. the ultimate bankruptcy is a dialogue of the most recent explorations of the response of rhodium-stabilized vinyl carbenoids with dienes.

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1997, 97, 523-596. ; Tam, W. Chem. Rev. 1996, 96, 49. 44 PAUL A. WENDER and JENNIFER A. LOVE 80. ; Natchus, M. ; Shuker, A. J. In TAXOL Science and Applications: M. ; CRC Press: New York, 1995, pp. 123-187. 81. Wender, P. ; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678. 82. Wender, P. ; Snapper, M. L. Tetrahedron Lett. 1987, 28, 2221. 83. Wender, P. ; Nuss, J. ; Smith, D. ; Bordner, J. J. Org. Chem. 1997, 62, 4908. 84. Wender, P. ; Correia, C. R. ; Ihle, N. C. J. Am. Chem. Soc. 1988,110, 5904. 85.

In the presence of 11 mol% Ni(COD)2 and 33 mol% PPh 3, for example, tetraene 1 undergoes a [4+4] cycloaddition 24 PAUL A. WENDER and JENNIFER A. LOVE to provide 2a and b in 70% yield as a 19:1 mixture of diastereomers, favoring the product with cis ring fusion (Eq. 53). ~ Ni(O)catalyst 211 2b (53) 1 E 3 ~. 4 for another new class of cycloadditions, the metal-catalyzed intramolecular [4+2] cycloaddition, this study also showed that variations in conditions can be used to preferentially produce a [4+2] cycloadduct (3).

39. Griesbeck, A. G. J. Prakt. Chem. 1993, 335, 489. 40. Wender, P. ; Eissenstat, M. ; Filosa, M. P. J. Am. Chem. Soc. 1979, 101, 2196. 41. Davies, H. M. ; Doan, B. D. J. Org. Chem. 1998, 63, 657. For additional examples of the scope of this reaction, see Davies, H. M. ; Matasi, J. ; Hodges, L. ; Huby, N. J. ; Houser, J. H. J. Org. Chem. 1997, 62, 1095. 42. Hemdon, J. ; Patel, P. ; Matasi, J. ; Tumer, S. ; Harp, J. ; Reid, M. D. J. Am. Chem. Soc. 1991, 113, 7808. 43. Funk, R. ; Olmstead, T. ; Parvez, M.

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