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(a) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 593-615.
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(c) Harmata, M. In Advances in Cycloaddition; Lautens, M., Ed.; JAI Press Inc.: Greenwich, 1997; Vol. 4, pp 41-86.
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5
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(a) Rigby, J. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 617-643.
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Rigby, J.H.1
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West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795.
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Koch, D.J.3
Kuehn, C.E.4
Arif, A.M.5
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8
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0001604648
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For recent examples, see: (a) Harmata, M.; Elomari, S. E.; Barnes, C. L. J. Am. Chem. Soc. 1996, 118, 2860. (b) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. (c) Cha, J. K.; Jin, S.-J.; Choi, J.-R.; Oh, J.; Lee, D. J. Am. Chem. Soc. 1995, 117, 10914. (d) Kim, H.; Ziani-Cherif, C.; Oh, J.; Cha, J. K. J. Org. Chem. 1995, 60, 792.
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Harmata, M.1
Elomari, S.E.2
Barnes, C.L.3
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9
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0000382832
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For recent examples, see: (a) Harmata, M.; Elomari, S. E.; Barnes, C. L. J. Am. Chem. Soc. 1996, 118, 2860. (b) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. (c) Cha, J. K.; Jin, S.-J.; Choi, J.-R.; Oh, J.; Lee, D. J. Am. Chem. Soc. 1995, 117, 10914. (d) Kim, H.; Ziani-Cherif, C.; Oh, J.; Cha, J. K. J. Org. Chem. 1995, 60, 792.
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Harmata, M.1
Elahmad, S.2
Barnes, C.L.3
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10
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0000235134
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For recent examples, see: (a) Harmata, M.; Elomari, S. E.; Barnes, C. L. J. Am. Chem. Soc. 1996, 118, 2860. (b) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. (c) Cha, J. K.; Jin, S.-J.; Choi, J.-R.; Oh, J.; Lee, D. J. Am. Chem. Soc. 1995, 117, 10914. (d) Kim, H.; Ziani-Cherif, C.; Oh, J.; Cha, J. K. J. Org. Chem. 1995, 60, 792.
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-
Cha, J.K.1
Jin, S.-J.2
Choi, J.-R.3
Oh, J.4
Lee, D.5
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11
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0000568170
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For recent examples, see: (a) Harmata, M.; Elomari, S. E.; Barnes, C. L. J. Am. Chem. Soc. 1996, 118, 2860. (b) Harmata, M.; Elahmad, S.; Barnes, C. L. J. Org. Chem. 1994, 59, 1241. (c) Cha, J. K.; Jin, S.-J.; Choi, J.-R.; Oh, J.; Lee, D. J. Am. Chem. Soc. 1995, 117, 10914. (d) Kim, H.; Ziani-Cherif, C.; Oh, J.; Cha, J. K. J. Org. Chem. 1995, 60, 792.
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J. Org. Chem.
, vol.60
, pp. 792
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Kim, H.1
Ziani-Cherif, C.2
Oh, J.3
Cha, J.K.4
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12
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0345520231
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(a) Bender, J. A.; Blize, A. E.; Browder, C. C.; Giese, S.; West, F. G. J. Org. Chem. 1998, 63, 2430.
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J. Org. Chem.
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Bender, J.A.1
Blize, A.E.2
Browder, C.C.3
Giese, S.4
West, F.G.5
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16
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0000710912
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(a) Ikeda, Y.; Ukai, J.; Ikeda, N.; Yamamoto, H. Tetrahedron 1987, 43, 723.
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(1987)
Tetrahedron
, vol.43
, pp. 723
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Ikeda, Y.1
Ukai, J.2
Ikeda, N.3
Yamamoto, H.4
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17
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13044252672
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Manuscript in preparation
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(b) Wang, Y.; West, F. G. Manuscript in preparation.
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Wang, Y.1
West, F.G.2
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18
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0029070308
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Aldehyde 3a had been prepared previously by other routes: (a) Craig, D.; Geach, N. J.; Pearson, C. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071. (b) Wulff, W. D.; Powers, T. S. J. Org. Chem. 1993, 58, 2381. (c) Smith, D. A.; Houk, K. N. Tetrahedron Lett. 1991, 32, 1549. (d) Segi, M.; Takahashi, M.; Nakajima, T.; Suga, S.; Sonoda, N. Synth. Commun. 1989, 19, 2431. (e) Oppolzer, W.; Dupuis, D. Tetrahedron Lett. 1985, 26, 5437. (f) Roush, W. R.; Hall, S. E. J. Am. Chem. Soc. 1981, 103, 5200.
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Tetrahedron
, vol.51
, pp. 6071
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Craig, D.1
Geach, N.J.2
Pearson, C.J.3
Slawin, A.M.Z.4
White, A.J.P.5
Williams, D.J.6
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19
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0000990451
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Aldehyde 3a had been prepared previously by other routes: (a) Craig, D.; Geach, N. J.; Pearson, C. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071. (b) Wulff, W. D.; Powers, T. S. J. Org. Chem. 1993, 58, 2381. (c) Smith, D. A.; Houk, K. N. Tetrahedron Lett. 1991, 32, 1549. (d) Segi, M.; Takahashi, M.; Nakajima, T.; Suga, S.; Sonoda, N. Synth. Commun. 1989, 19, 2431. (e) Oppolzer, W.; Dupuis, D. Tetrahedron Lett. 1985, 26, 5437. (f) Roush, W. R.; Hall, S. E. J. Am. Chem. Soc. 1981, 103, 5200.
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Wulff, W.D.1
Powers, T.S.2
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20
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0025979634
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-
Aldehyde 3a had been prepared previously by other routes: (a) Craig, D.; Geach, N. J.; Pearson, C. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071. (b) Wulff, W. D.; Powers, T. S. J. Org. Chem. 1993, 58, 2381. (c) Smith, D. A.; Houk, K. N. Tetrahedron Lett. 1991, 32, 1549. (d) Segi, M.; Takahashi, M.; Nakajima, T.; Suga, S.; Sonoda, N. Synth. Commun. 1989, 19, 2431. (e) Oppolzer, W.; Dupuis, D. Tetrahedron Lett. 1985, 26, 5437. (f) Roush, W. R.; Hall, S. E. J. Am. Chem. Soc. 1981, 103, 5200.
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Tetrahedron Lett.
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, pp. 1549
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Smith, D.A.1
Houk, K.N.2
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21
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2042509094
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Aldehyde 3a had been prepared previously by other routes: (a) Craig, D.; Geach, N. J.; Pearson, C. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071. (b) Wulff, W. D.; Powers, T. S. J. Org. Chem. 1993, 58, 2381. (c) Smith, D. A.; Houk, K. N. Tetrahedron Lett. 1991, 32, 1549. (d) Segi, M.; Takahashi, M.; Nakajima, T.; Suga, S.; Sonoda, N. Synth. Commun. 1989, 19, 2431. (e) Oppolzer, W.; Dupuis, D. Tetrahedron Lett. 1985, 26, 5437. (f) Roush, W. R.; Hall, S. E. J. Am. Chem. Soc. 1981, 103, 5200.
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Synth. Commun.
, vol.19
, pp. 2431
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Segi, M.1
Takahashi, M.2
Nakajima, T.3
Suga, S.4
Sonoda, N.5
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22
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0001350319
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Aldehyde 3a had been prepared previously by other routes: (a) Craig, D.; Geach, N. J.; Pearson, C. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071. (b) Wulff, W. D.; Powers, T. S. J. Org. Chem. 1993, 58, 2381. (c) Smith, D. A.; Houk, K. N. Tetrahedron Lett. 1991, 32, 1549. (d) Segi, M.; Takahashi, M.; Nakajima, T.; Suga, S.; Sonoda, N. Synth. Commun. 1989, 19, 2431. (e) Oppolzer, W.; Dupuis, D. Tetrahedron Lett. 1985, 26, 5437. (f) Roush, W. R.; Hall, S. E. J. Am. Chem. Soc. 1981, 103, 5200.
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Tetrahedron Lett.
, vol.26
, pp. 5437
-
-
Oppolzer, W.1
Dupuis, D.2
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23
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0000543215
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Aldehyde 3a had been prepared previously by other routes: (a) Craig, D.; Geach, N. J.; Pearson, C. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071. (b) Wulff, W. D.; Powers, T. S. J. Org. Chem. 1993, 58, 2381. (c) Smith, D. A.; Houk, K. N. Tetrahedron Lett. 1991, 32, 1549. (d) Segi, M.; Takahashi, M.; Nakajima, T.; Suga, S.; Sonoda, N. Synth. Commun. 1989, 19, 2431. (e) Oppolzer, W.; Dupuis, D. Tetrahedron Lett. 1985, 26, 5437. (f) Roush, W. R.; Hall, S. E. J. Am. Chem. Soc. 1981, 103, 5200.
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J. Am. Chem. Soc.
, vol.103
, pp. 5200
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Roush, W.R.1
Hall, S.E.2
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24
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33845554840
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3 in silicon-directed Nazarov reactions, see: Denmark, S. E.; Jones, T. K. J. Am. Chem. Soc. 1982, 104, 2642. Other Lewis acids: (b) Tsuge, O.; Kanemasa, S.; Fujiwara, I.; Wada, E. Bull. Chem. Soc. Jpn. 1987, 60, 325. (c) Santelli, M.; Dulcere, J.-P.; Morel-Fourrier, C. J. Am. Chem. Soc. 1991, 113, 8062. (d) Marino, J. P.; Linderman, R. J. J. Org. Chem. 1981, 46, 3696.
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(1982)
J. Am. Chem. Soc.
, vol.104
, pp. 2642
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Denmark, S.E.1
Jones, T.K.2
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25
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13044296871
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3 in silicon-directed Nazarov reactions, see: Denmark, S. E.; Jones, T. K. J. Am. Chem. Soc. 1982, 104, 2642. Other Lewis acids: (b) Tsuge, O.; Kanemasa, S.; Fujiwara, I.; Wada, E. Bull. Chem. Soc. Jpn. 1987, 60, 325. (c) Santelli, M.; Dulcere, J.-P.; Morel-Fourrier, C. J. Am. Chem. Soc. 1991, 113, 8062. (d) Marino, J. P.; Linderman, R. J. J. Org. Chem. 1981, 46, 3696.
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Bull. Chem. Soc. Jpn.
, vol.60
, pp. 325
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Tsuge, O.1
Kanemasa, S.2
Fujiwara, I.3
Wada, E.4
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26
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0001753423
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3 in silicon-directed Nazarov reactions, see: Denmark, S. E.; Jones, T. K. J. Am. Chem. Soc. 1982, 104, 2642. Other Lewis acids: (b) Tsuge, O.; Kanemasa, S.; Fujiwara, I.; Wada, E. Bull. Chem. Soc. Jpn. 1987, 60, 325. (c) Santelli, M.; Dulcere, J.-P.; Morel-Fourrier, C. J. Am. Chem. Soc. 1991, 113, 8062. (d) Marino, J. P.; Linderman, R. J. J. Org. Chem. 1981, 46, 3696.
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J. Am. Chem. Soc.
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, pp. 8062
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Santelli, M.1
Dulcere, J.-P.2
Morel-Fourrier, C.3
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27
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33845556090
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3 in silicon-directed Nazarov reactions, see: Denmark, S. E.; Jones, T. K. J. Am. Chem. Soc. 1982, 104, 2642. Other Lewis acids: (b) Tsuge, O.; Kanemasa, S.; Fujiwara, I.; Wada, E. Bull. Chem. Soc. Jpn. 1987, 60, 325. (c) Santelli, M.; Dulcere, J.-P.; Morel-Fourrier, C. J. Am. Chem. Soc. 1991, 113, 8062. (d) Marino, J. P.; Linderman, R. J. J. Org. Chem. 1981, 46, 3696.
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J. Org. Chem.
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, pp. 3696
-
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Marino, J.P.1
Linderman, R.J.2
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28
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13044286620
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5b
-
5b
-
-
-
-
29
-
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13044251042
-
-
note
-
(a) The stereochemistry of 7a and 8a was assigned based on close spectral analogy to 7b and 8b. (b) The stereochemistry of 8d was rigorously determined by X-ray diffraction analysis, and that of 8c was assigned based on close spectral analogy to 8d.
-
-
-
-
30
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0027754140
-
-
Endo and exo refer to the orientation of the diene in relation to the central carbon of the oxyallyl unit. There is some precedent for greater exo/ endo selectivity in intramolecular [4+3]- and [4+4]-cycloadditions: (a) Harmata, M.; Herron, B. F. J. Org. Chem. 1993, 58, 7393. (b) Sieburth, S. McN.; Hiel, G.; Lin, C.-H.; Kuan, D. P. J. Org. Chem. 1994, 59, 80. (c) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J. J. Am. Chem. Soc. 1996, 118, 10803.
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(1993)
J. Org. Chem.
, vol.58
, pp. 7393
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Harmata, M.1
Herron, B.F.2
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31
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0028280575
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-
Endo and exo refer to the orientation of the diene in relation to the central carbon of the oxyallyl unit. There is some precedent for greater exo/ endo selectivity in intramolecular [4+3]- and [4+4]-cycloadditions: (a) Harmata, M.; Herron, B. F. J. Org. Chem. 1993, 58, 7393. (b) Sieburth, S. McN.; Hiel, G.; Lin, C.-H.; Kuan, D. P. J. Org. Chem. 1994, 59, 80. (c) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J. J. Am. Chem. Soc. 1996, 118, 10803.
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(1994)
J. Org. Chem.
, vol.59
, pp. 80
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Sieburth, S.McN.1
Hiel, G.2
Lin, C.-H.3
Kuan, D.P.4
-
32
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0000382422
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Endo and exo refer to the orientation of the diene in relation to the central carbon of the oxyallyl unit. There is some precedent for greater exo/ endo selectivity in intramolecular [4+3]- and [4+4]-cycloadditions: (a) Harmata, M.; Herron, B. F. J. Org. Chem. 1993, 58, 7393. (b) Sieburth, S. McN.; Hiel, G.; Lin, C.-H.; Kuan, D. P. J. Org. Chem. 1994, 59, 80. (c) Sieburth, S. McN.; Chen, J.; Ravindran, K.; Chen, J. J. Am. Chem. Soc. 1996, 118, 10803.
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(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 10803
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Sieburth, S.McN.1
Chen, J.2
Ravindran, K.3
Chen, J.4
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35
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0002863020
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Takano, S.; Inomata, K.; Samizu, K.; Tomita, S.; Yanase, M.; Suzuki, M.; Iwabuchi, Y.; Sugihara, T.; Ogasawara, K. Chem. Lett. 1989, 1283. The reaction was not complete after stirring for 3 days following the literature procedure; however, we have found that the reaction went to completion in 12 h in the presence of silica gel.
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(1989)
Chem. Lett.
, pp. 1283
-
-
Takano, S.1
Inomata, K.2
Samizu, K.3
Tomita, S.4
Yanase, M.5
Suzuki, M.6
Iwabuchi, Y.7
Sugihara, T.8
Ogasawara, K.9
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