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Volumn 62, Issue 22, 1997, Pages 7858-7862

A Novel Palladium-Mediated Cascade Reaction Triggered by Strain Release of the Cyclobutane System. A New General Route to Benzo- And Naphthohydrindans

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EID: 1542500662     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971377z     Document Type: Article
Times cited : (3)

References (92)
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    • Trost, B.M.1    Pfrengle, W.2    Urabe, H.3    Dumas, J.4
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    • For recent works in this area, see: (a) Luo, F. T.; Chou, F. L.; Wang, R. T. J. Org. Chem. 1990, 55, 4846-4849. (b) Negishi, E.; Noda, Y.; Lamaty, F.; Vawter, E. J. Tetrahedron Lett. 1990, 31, 4393-4396. (c) Nuss, J. M.; Levine, B. H.; Rennels, R. A.; Heravi, M. M. Tetrahedron Lett. 1991, 32, 5243-5246. (d) Trost, B. M.; Pfrengle, W.; Urabe, H.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1923-1924. (e) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1992, 114, 791-792. (f) Negishi, E.; Harring, L. S.; Owczarczyk, Z.; Mohamud, M. M.; Ay, M. Tetrahedron Lett. 1992, 33, 3253-3256. (g) Takacs, J. M.; Zhu, J.; Chandramouli, S. J. Am. Chem. Soc. 1992, 114, 773-774. (h) Nuss, J. M.; Murphy, M. M.; Rennels, R. A.; Heravi, M. H.; Mohr, B. J. Tetrahedron Lett. 1993, 34, 3079-3082. (i) Kucera, D. J.; O'Connor, S. J.; Overman, L. E. J. Org. Chem. 1993, 58, 5304-5306. (j) Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 157-160. (k) Trost, B. M.; Gelling, O. T. Tetrahedron Lett. 1993, 34, 8233-8236. (l) Trost, B. M.; Czeskis, B. A. Tetrahedron Lett. 1994, 35, 211-214. (m) Trost, B. M.; Parquette, J. R.; Marquart, A. L. J. Am. Chem. Soc. 1995, 117, 3284-3285. (n) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156-5157. (o) Trost, B. M.; McIntosh, M. C. J. Am. Chem. Soc. 1995, 117, 7255-7256.
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    • Trost, B.M.1    Shi, Y.2
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    • For recent works in this area, see: (a) Luo, F. T.; Chou, F. L.; Wang, R. T. J. Org. Chem. 1990, 55, 4846-4849. (b) Negishi, E.; Noda, Y.; Lamaty, F.; Vawter, E. J. Tetrahedron Lett. 1990, 31, 4393-4396. (c) Nuss, J. M.; Levine, B. H.; Rennels, R. A.; Heravi, M. M. Tetrahedron Lett. 1991, 32, 5243-5246. (d) Trost, B. M.; Pfrengle, W.; Urabe, H.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1923-1924. (e) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1992, 114, 791-792. (f) Negishi, E.; Harring, L. S.; Owczarczyk, Z.; Mohamud, M. M.; Ay, M. Tetrahedron Lett. 1992, 33, 3253-3256. (g) Takacs, J. M.; Zhu, J.; Chandramouli, S. J. Am. Chem. Soc. 1992, 114, 773-774. (h) Nuss, J. M.; Murphy, M. M.; Rennels, R. A.; Heravi, M. H.; Mohr, B. J. Tetrahedron Lett. 1993, 34, 3079-3082. (i) Kucera, D. J.; O'Connor, S. J.; Overman, L. E. J. Org. Chem. 1993, 58, 5304-5306. (j) Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 157-160. (k) Trost, B. M.; Gelling, O. T. Tetrahedron Lett. 1993, 34, 8233-8236. (l) Trost, B. M.; Czeskis, B. A. Tetrahedron Lett. 1994, 35, 211-214. (m) Trost, B. M.; Parquette, J. R.; Marquart, A. L. J. Am. Chem. Soc. 1995, 117, 3284-3285. (n) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156-5157. (o) Trost, B. M.; McIntosh, M. C. J. Am. Chem. Soc. 1995, 117, 7255-7256.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 3253-3256
    • Negishi, E.1    Harring, L.S.2    Owczarczyk, Z.3    Mohamud, M.M.4    Ay, M.5
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    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 773-774
    • Takacs, J.M.1    Zhu, J.2    Chandramouli, S.3
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    • (1993) Tetrahedron Lett. , vol.34 , pp. 3079-3082
    • Nuss, J.M.1    Murphy, M.M.2    Rennels, R.A.3    Heravi, M.H.4    Mohr, B.J.5
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    • (1993) J. Org. Chem. , vol.58 , pp. 5304-5306
    • Kucera, D.J.1    O'Connor, S.J.2    Overman, L.E.3
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    • For recent works in this area, see: (a) Luo, F. T.; Chou, F. L.; Wang, R. T. J. Org. Chem. 1990, 55, 4846-4849. (b) Negishi, E.; Noda, Y.; Lamaty, F.; Vawter, E. J. Tetrahedron Lett. 1990, 31, 4393-4396. (c) Nuss, J. M.; Levine, B. H.; Rennels, R. A.; Heravi, M. M. Tetrahedron Lett. 1991, 32, 5243-5246. (d) Trost, B. M.; Pfrengle, W.; Urabe, H.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1923-1924. (e) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1992, 114, 791-792. (f) Negishi, E.; Harring, L. S.; Owczarczyk, Z.; Mohamud, M. M.; Ay, M. Tetrahedron Lett. 1992, 33, 3253-3256. (g) Takacs, J. M.; Zhu, J.; Chandramouli, S. J. Am. Chem. Soc. 1992, 114, 773-774. (h) Nuss, J. M.; Murphy, M. M.; Rennels, R. A.; Heravi, M. H.; Mohr, B. J. Tetrahedron Lett. 1993, 34, 3079-3082. (i) Kucera, D. J.; O'Connor, S. J.; Overman, L. E. J. Org. Chem. 1993, 58, 5304-5306. (j) Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 157-160. (k) Trost, B. M.; Gelling, O. T. Tetrahedron Lett. 1993, 34, 8233-8236. (l) Trost, B. M.; Czeskis, B. A. Tetrahedron Lett. 1994, 35, 211-214. (m) Trost, B. M.; Parquette, J. R.; Marquart, A. L. J. Am. Chem. Soc. 1995, 117, 3284-3285. (n) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156-5157. (o) Trost, B. M.; McIntosh, M. C. J. Am. Chem. Soc. 1995, 117, 7255-7256.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 157-160
    • Brown, S.1    Clarkson, S.2    Grigg, R.3    Sridharan, V.4
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    • For recent works in this area, see: (a) Luo, F. T.; Chou, F. L.; Wang, R. T. J. Org. Chem. 1990, 55, 4846-4849. (b) Negishi, E.; Noda, Y.; Lamaty, F.; Vawter, E. J. Tetrahedron Lett. 1990, 31, 4393-4396. (c) Nuss, J. M.; Levine, B. H.; Rennels, R. A.; Heravi, M. M. Tetrahedron Lett. 1991, 32, 5243-5246. (d) Trost, B. M.; Pfrengle, W.; Urabe, H.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1923-1924. (e) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1992, 114, 791-792. (f) Negishi, E.; Harring, L. S.; Owczarczyk, Z.; Mohamud, M. M.; Ay, M. Tetrahedron Lett. 1992, 33, 3253-3256. (g) Takacs, J. M.; Zhu, J.; Chandramouli, S. J. Am. Chem. Soc. 1992, 114, 773-774. (h) Nuss, J. M.; Murphy, M. M.; Rennels, R. A.; Heravi, M. H.; Mohr, B. J. Tetrahedron Lett. 1993, 34, 3079-3082. (i) Kucera, D. J.; O'Connor, S. J.; Overman, L. E. J. Org. Chem. 1993, 58, 5304-5306. (j) Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 157-160. (k) Trost, B. M.; Gelling, O. T. Tetrahedron Lett. 1993, 34, 8233-8236. (l) Trost, B. M.; Czeskis, B. A. Tetrahedron Lett. 1994, 35, 211-214. (m) Trost, B. M.; Parquette, J. R.; Marquart, A. L. J. Am. Chem. Soc. 1995, 117, 3284-3285. (n) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156-5157. (o) Trost, B. M.; McIntosh, M. C. J. Am. Chem. Soc. 1995, 117, 7255-7256.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 8233-8236
    • Trost, B.M.1    Gelling, O.T.2
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    • For recent works in this area, see: (a) Luo, F. T.; Chou, F. L.; Wang, R. T. J. Org. Chem. 1990, 55, 4846-4849. (b) Negishi, E.; Noda, Y.; Lamaty, F.; Vawter, E. J. Tetrahedron Lett. 1990, 31, 4393-4396. (c) Nuss, J. M.; Levine, B. H.; Rennels, R. A.; Heravi, M. M. Tetrahedron Lett. 1991, 32, 5243-5246. (d) Trost, B. M.; Pfrengle, W.; Urabe, H.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1923-1924. (e) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1992, 114, 791-792. (f) Negishi, E.; Harring, L. S.; Owczarczyk, Z.; Mohamud, M. M.; Ay, M. Tetrahedron Lett. 1992, 33, 3253-3256. (g) Takacs, J. M.; Zhu, J.; Chandramouli, S. J. Am. Chem. Soc. 1992, 114, 773-774. (h) Nuss, J. M.; Murphy, M. M.; Rennels, R. A.; Heravi, M. H.; Mohr, B. J. Tetrahedron Lett. 1993, 34, 3079-3082. (i) Kucera, D. J.; O'Connor, S. J.; Overman, L. E. J. Org. Chem. 1993, 58, 5304-5306. (j) Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 157-160. (k) Trost, B. M.; Gelling, O. T. Tetrahedron Lett. 1993, 34, 8233-8236. (l) Trost, B. M.; Czeskis, B. A. Tetrahedron Lett. 1994, 35, 211-214. (m) Trost, B. M.; Parquette, J. R.; Marquart, A. L. J. Am. Chem. Soc. 1995, 117, 3284-3285. (n) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156-5157. (o) Trost, B. M.; McIntosh, M. C. J. Am. Chem. Soc. 1995, 117, 7255-7256.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 211-214
    • Trost, B.M.1    Czeskis, B.A.2
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    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 3284-3285
    • Trost, B.M.1    Parquette, J.R.2    Marquart, A.L.3
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    • For cyclic cascade carbopalladations, see: (a) Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328-2329. (b) Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5846-5848. (c) Zhang, Y.; Wu, G.; Agnel, G.; Negishi, E. J. Am. Chem. Soc. 1990, 112, 8590-8592. (d) Grigg, R.; Dorrity, M. J.; Malone, J. F.; Sridharan, V.; Sukirthalingam, S. Tetrahedron Lett. 1990, 31, 1343-1346. (e) Meyer, F. E.; de Meijere, A. Synlett 1991, 777-778. (f) Meyer, F. E.; Parsons, P. J.; de Meijere, A. J. Org. Chem. 1991, 56, 6487-6488. (g) Negishi, E.; Marring, L. S.; Owczarczyk, Z.; Mohamud, M. M.; Ay, M. Tetrahedron Lett. 1992, 33, 3253-3256. (h) Negishi, E.; Ay, M.; Sugihara, T. Tetrahedron 1993, 49, 5471-5482. Sugihara, T.; Copéret, C.; Owczarczyk, Z.; Marring, L. S.; Negishi, E. J. Am. Chem. Soc. 1994, 116, 7923-7924.
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    • For recent studies on the synthesis of benzohydrindans and their transformation into various types of biologically important steroids, see: (a) Nemoto, H.; Ando, M.; Fukumoto, K. Tetrahedron Lett. 1990, 31, 6205-6208. (b) Nemoto, H.; Matsuhashi, N.; Imaizumi, M.; Nagai, M.; Fukumoto, K. J. Org. Chem. 1990, 55, 5625-5631. (c) Nemoto, H.; Satoh, A.; Ando, M.; Fukumoto, K. J. Chem. Soc., Chem. Commun. 1990, 1001-1002; J. Chem. Soc., Perkin Trans. 1 1991, 1309-1314. (d) Nemoto, H.; Matsuhashi, N.; Satoh, A.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1992, 495-498. (e) Nemoto, H.; Satoh, A.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1993, 2237-2238. (f) Nemoto, H.; Satoh, A.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1994, 943-946. (g) Nemoto, H.; Satoh, A.; Fukui, H.; Fujimori, S.; Fukumoto, K. Chem. Pharm. Bull. 1994, 42, 1963-1965. (h) Nemoto, H.; Satoh, A.; Fukumoto, K.; Kabuto, C. J. Org. Chem. 1995, 60, 594-600. (i) Nemoto, H.; Satoh, A.; Fukumoto, K. Tetrahedron 1995, 51, 10159-10174. (j) Nemoto, H.; Satoh, A.; Fukumoto, K. Synlett 1995, 199-200.
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    • note
    • The stereochemistry of 17, 24, 31, and 37 was confirmed by the observation of the definite NOE between methyl protons of isopropenyl group and adjacent methine proton in these NMR spectra, which were observed at 1.83 and 3.95 ppm for 17, 1.85 and 4.17 ppm for 24, 1.84 and 4.12-4.19 ppm for 31, and 1.84 and 4.30 ppm for 37, respectively.
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    • Brown, W.L.1    Fallis, A.G.2
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    • note
    • The stereochemistry of these product in Tables 1-3 was confirmed by the observation of the definite NOE between methyl and methine protons at angular positions in these NMR spectra, which were observed at 1.07 and 3.05 ppm for 47, 1.04 and 3.01 ppm for 49, 1.01 and 3.12 ppm for 51, 1.01 and 2.96 ppm for 53, 1.14 and 3.13-3.22 ppm for 55i, 1.03 and 2.92-3.01 ppm for 57i, 1.19 and 3.32 ppm for 59, and 1.15 and 3.07 ppm for 61, respectively. In addition to these data, the general tendencies that the angular methyl group of this type of trans-benzohydrindan resonates at higher field than that of corresponding cis isomer in its NMR spectrum because of the shielding effect of aromatic ring have been recognized (see ref 6).
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    • Larock, R. C.; Hightower, T. R.; Kraus, G. A.; Hahn, P.; Zheng, D. Tetrahedron Lett. 1995, 36, 2423-2426. Under this condition, the enone 62 was produced in 22% yield beside the cascade products 54-57. The structure of 62 was characterized as its deprotected derivative 62I.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 2423-2426
    • Larock, R.C.1    Hightower, T.R.2    Kraus, G.A.3    Hahn, P.4    Zheng, D.5


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