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1
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0000097153
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For recent reviews, see: (a) Evans, D. A,; Johnson, J. S. Compr. Asymm. Catal. 1999, 3, 1177.
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(1999)
Compr. Asymm. Catal.
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Evans, D.A.1
Johnson, J.S.2
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5
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0000210159
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Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812.
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J. Am. Chem. Soc.
, vol.116
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Mikami, K.1
Motoyama, Y.2
Terada, M.3
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6
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0000234134
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Previous syntheses of (±)-1: (a) Büchi, G.; Coffen, D. L.; Kocsis, K.; Sonnet, P. E.; Ziegler, F. E. J. Am. Chem. Soc. 1965, 87, 2073.
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(1965)
J. Am. Chem. Soc.
, vol.87
, pp. 2073
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Büchi, G.1
Coffen, D.L.2
Kocsis, K.3
Sonnet, P.E.4
Ziegler, F.E.5
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7
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0001068819
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(b) Büchi, G.; Coffen, D. L.; Kocsis, K.; Sonnet, P. E.; Ziegler, F. E. J. Am. Chem. Soc. 1966, 88, 3099.
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J. Am. Chem. Soc.
, vol.88
, pp. 3099
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Büchi, G.1
Coffen, D.L.2
Kocsis, K.3
Sonnet, P.E.4
Ziegler, F.E.5
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9
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0014412475
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(d) Nagata, W.; Hirai, S.; Okumura, T.; Kawata, K. J. Am. Chem. Soc. 1968, 90, 1650.
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J. Am. Chem. Soc.
, vol.90
, pp. 1650
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Nagata, W.1
Hirai, S.2
Okumura, T.3
Kawata, K.4
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10
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0011254323
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(e) Ikezaki, M.; Wakamatsu, T.; Ban, Y. J. Chem. Soc., Chem. Commun. 1969, 88.
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(1969)
J. Chem. Soc., Chem. Commun.
, pp. 88
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Ikezaki, M.1
Wakamatsu, T.2
Ban, Y.3
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11
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84980146027
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(f) Rosenmund, P.; Haase, W. H.; Bauer, J.; Frische, R. Chem. Ber. 1975, 108, 1871.
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(1975)
Chem. Ber.
, vol.108
, pp. 1871
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Rosenmund, P.1
Haase, W.H.2
Bauer, J.3
Frische, R.4
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13
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85004247144
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(h) Imanishi, T.; Yagi, N.; Hanaoka, M. Chem. Pharm. Bull. 1985, 33,. 4202.
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(1985)
Chem. Pharm. Bull.
, vol.33
, pp. 4202
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Imanishi, T.1
Yagi, N.2
Hanaoka, M.3
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14
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0001593492
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Huffman, J. W.; Shanmugasundaram, G.; Sawdaye, R.; Raveendranath, P. C.; Desai, R. C. J. Org. Chem. 1985, 50, 1460.
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(1985)
J. Org. Chem.
, vol.50
, pp. 1460
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Huffman, J.W.1
Shanmugasundaram, G.2
Sawdaye, R.3
Raveendranath, P.C.4
Desai, R.C.5
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17
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0030580371
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Henry, K. J., Jr.; Grieco, P. A.; Dubay, W. J. Tetrahedron Lett. 1996, 37, 8289.
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(1996)
Tetrahedron Lett.
, vol.37
, pp. 8289
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Henry K.J. Jr.1
2
Grieco, P.A.3
Dubay, W.J.4
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18
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33947092471
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An asymmetric synthesis leading to an 80:20 mixture of enantiomers of ibogamine favoring (+)-1 was accomplished by Trost (see Trost, B. M.; Godleski, S. A.; Genet, J. P. J. Am. Chem. Soc. 1978, 100, 3930).
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(1978)
J. Am. Chem. Soc.
, vol.100
, pp. 3930
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Trost, B.M.1
Godleski, S.A.2
Genet, J.P.3
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25
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33845183220
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Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
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(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 5340
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Narasaka, K.1
Iwasawa, N.2
Inoue, M.3
Yamada, T.4
Nakashima, M.5
Sugimori, J.6
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26
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33845376028
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Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370.
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J. Org. Chem.
, vol.51
, pp. 2370
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Trost, B.M.1
Belletire, J.L.2
Godleski, S.3
McDougal, P.G.4
Balkovec, J.M.5
Baldwin, J.J.6
Christy, M.E.7
Ponticello, G.S.8
Varga, S.L.9
Springer, J.P.10
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27
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0042881491
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note
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It is noteworthy that the absolute configuration of 5 corresponds to that observed by Mikami (ref 3) for the Diels-Alder adduct obtained from the reaction of 1-methoxybutadiene with naphthoquinone catalyzed by (S)-4.
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28
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84962359450
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For a contemporary view of the classical Beckmann rearrangement, see: Nguyen, M. T.; Raspoet, G.; Vanquickenborne, L. G. J. Am. Chem. Soc. 1997, 119, 2552.
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(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 2552
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Nguyen, M.T.1
Raspoet, G.2
Vanquickenborne, L.G.3
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30
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0030941221
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(b) For an application to alkaloid synthesis, see: Simon, Cs.; Hosztafi, S.; Makleit, S. J. Heterocycl. Chem. 1997, 34, 349.
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(1997)
J. Heterocycl. Chem.
, vol.34
, pp. 349
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Simon, Cs.1
Hosztafi, S.2
Makleit, S.3
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33
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0032482284
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Sundberg, R. J.; Hong, J.; Smith, S. Q.; Sabat, M. Tetrahedron 1998, 54, 6259.
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(1998)
Tetrahedron
, vol.54
, pp. 6259
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Sundberg, R.J.1
Hong, J.2
Smith, S.Q.3
Sabat, M.4
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34
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0000258740
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Dickel, D. F.; Holden, C. L.; Maxfield, R. C.; Paszek, L. E.; Taylor, W. I. J. Am. Chem. Soc. 1958, 80, 123.
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(1958)
J. Am. Chem. Soc.
, vol.80
, pp. 123
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Dickel, D.F.1
Holden, C.L.2
Maxfield, R.C.3
Paszek, L.E.4
Taylor, W.I.5
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35
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0041879319
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note
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No evidence for a charge-transfer band was found in the UV-visible spectrum of a mixture of 4 and benzoquinone. However, the solution containing these compounds was an intense red-brown color.
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