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(a) Hudrlik, P. F.; Peterson, D.; Rona, R. J. J. Org. Chem. 1975, 40, 2263-2264.
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Hudrlik, P.F.1
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Rona, R.J.3
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3
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(b) Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
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Rona, R.J.3
Misra, R.N.4
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4
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(c) Hudrlik, P. F.; Hudrlik, A. M.; Kulkarni, A. K. Tetrahedron Lett. 1985, 26, 139-142.
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Tetrahedron Lett.
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Kulkarni, A.K.3
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2a,3 anti-elimination by conversion of the hydroxyl to a good leaving group and treatment with fluoride, e.g., see: (a) Luo, F.-T.; Negishi, E. J. Org. Chem. 1983, 48, 5144-5146. See also: (b) Croudace, M. C.; Schore, N. E. J. Org. Chem. 1981, 46, 5357-5363.
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Luo, F.-T.1
Negishi, E.2
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7
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0012021395
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2a,3 anti-elimination by conversion of the hydroxyl to a good leaving group and treatment with fluoride, e.g., see: (a) Luo, F.-T.; Negishi, E. J. Org. Chem. 1983, 48, 5144-5146. See also: (b) Croudace, M. C.; Schore, N. E. J. Org. Chem. 1981, 46, 5357-5363.
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Croudace, M.C.1
Schore, N.E.2
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8
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0000449963
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Kitano, Y.; Matsumoto, T.; Sato, F. Tetrahedron 1988, 44, 4073-4086. Carlier, P. R.; Mungall, W. S.; Schröder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 2978-2979. This topic is reviewed in ref 1.
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Sato, F.3
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9
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0000560497
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Kitano, Y.; Matsumoto, T.; Sato, F. Tetrahedron 1988, 44, 4073-4086. Carlier, P. R.; Mungall, W. S.; Schröder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 2978-2979. This topic is reviewed in ref 1.
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Carlier, P.R.1
Mungall, W.S.2
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11
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3643145613
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Many other examples including (b) Robbins, C. M.; Whitham, G. H. J. Chem. Soc. D 1976, 697-698. (c) Fristad, W. E.; Bailey, T. R.; Paquette, L. A. J. Org. Chem. 1980, 45, 3028-3037. (d) Davis, A. P.; Hughes, G. J.; Lowndes, P. R.; Robbins, C. M.; Thomas, E. J.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1981, 1934-1941. (e) Takeda, Y.; Matsumoto, T.; Sato, F. J. Org. Chem. 1986, 51, 4728-4731. (f) Hudrlik, P. F.; Agwaramgbo, E. L. O.; Hudrlik, A. M. J. Org. Chem. 1989, 54, 5613-5618.
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Robbins, C.M.1
Whitham, G.H.2
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12
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0000928817
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-
Many other examples including (b) Robbins, C. M.; Whitham, G. H. J. Chem. Soc. D 1976, 697-698. (c) Fristad, W. E.; Bailey, T. R.; Paquette, L. A. J. Org. Chem. 1980, 45, 3028-3037. (d) Davis, A. P.; Hughes, G. J.; Lowndes, P. R.; Robbins, C. M.; Thomas, E. J.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1981, 1934-1941. (e) Takeda, Y.; Matsumoto, T.; Sato, F. J. Org. Chem. 1986, 51, 4728-4731. (f) Hudrlik, P. F.; Agwaramgbo, E. L. O.; Hudrlik, A. M. J. Org. Chem. 1989, 54, 5613-5618.
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Fristad, W.E.1
Bailey, T.R.2
Paquette, L.A.3
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13
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37049096641
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-
Many other examples including (b) Robbins, C. M.; Whitham, G. H. J. Chem. Soc. D 1976, 697-698. (c) Fristad, W. E.; Bailey, T. R.; Paquette, L. A. J. Org. Chem. 1980, 45, 3028-3037. (d) Davis, A. P.; Hughes, G. J.; Lowndes, P. R.; Robbins, C. M.; Thomas, E. J.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1981, 1934-1941. (e) Takeda, Y.; Matsumoto, T.; Sato, F. J. Org. Chem. 1986, 51, 4728-4731. (f) Hudrlik, P. F.; Agwaramgbo, E. L. O.; Hudrlik, A. M. J. Org. Chem. 1989, 54, 5613-5618.
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J. Chem. Soc., Perkin Trans. 1
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Davis, A.P.1
Hughes, G.J.2
Lowndes, P.R.3
Robbins, C.M.4
Thomas, E.J.5
Whitham, G.H.6
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14
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0001210758
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Many other examples including (b) Robbins, C. M.; Whitham, G. H. J. Chem. Soc. D 1976, 697-698. (c) Fristad, W. E.; Bailey, T. R.; Paquette, L. A. J. Org. Chem. 1980, 45, 3028-3037. (d) Davis, A. P.; Hughes, G. J.; Lowndes, P. R.; Robbins, C. M.; Thomas, E. J.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1981, 1934-1941. (e) Takeda, Y.; Matsumoto, T.; Sato, F. J. Org. Chem. 1986, 51, 4728-4731. (f) Hudrlik, P. F.; Agwaramgbo, E. L. O.; Hudrlik, A. M. J. Org. Chem. 1989, 54, 5613-5618.
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J. Org. Chem.
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Takeda, Y.1
Matsumoto, T.2
Sato, F.3
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15
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0024826190
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Many other examples including (b) Robbins, C. M.; Whitham, G. H. J. Chem. Soc. D 1976, 697-698. (c) Fristad, W. E.; Bailey, T. R.; Paquette, L. A. J. Org. Chem. 1980, 45, 3028-3037. (d) Davis, A. P.; Hughes, G. J.; Lowndes, P. R.; Robbins, C. M.; Thomas, E. J.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1981, 1934-1941. (e) Takeda, Y.; Matsumoto, T.; Sato, F. J. Org. Chem. 1986, 51, 4728-4731. (f) Hudrlik, P. F.; Agwaramgbo, E. L. O.; Hudrlik, A. M. J. Org. Chem. 1989, 54, 5613-5618.
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J. Org. Chem.
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Hudrlik, P.F.1
Agwaramgbo, E.L.O.2
Hudrlik, A.M.3
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17
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37049076932
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(b) Kitano, Y., Matsumoto, T; Sato, F. J. Chem. Soc., Chem. Commun. 1986, 1323-1325.
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(c) Tamao, K.; Najako, E.; Ito, Y. J. Org. Chem. 1987, 52, 4412-4414.
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(e) Alexakis, A.; Mangeney, P.; Ghribi, A.; Jachiet, D.; Normant, J. F. Philos. Trans. R. Soc. London, Ser. A 1988, 326, 557-564.
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Alexakis, A.1
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(g) Chou, S.-S. P.; Kuo, H.-L.; Wang, C.-J.; Tsai, C.-Y.; Sun, C.-M. J. Org. Chem. 1989, 54, 868-872.
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(h) Zhang, Y.; Miller, J. A.; Negishi, E. J. Org. Chem. 1989, 54, 2043-2044.
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(j) Shimizu, N.; Imazu, S.; Shibata, F.; Tsuno, Y. Bull. Chem. Soc. Jpn. 1991, 64, 1122-1128.
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(c) Eisch, J. J.; Liu, Z.-R.; Singh, M. J. Org. Chem. 1992, 57, 1618-1621.
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(a) Yamamoto, K.; Kimura, T.; Tomo, Y. Tetrahedron Lett. 1984, 25, 2155-2158.
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Okamoto, S.; Shimazaki, T.; Kobayashi, Y.; Sato, F. Tetrahedron Lett. 1987, 28, 2033-2036.
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20844449627
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(a) Hudrlik, P. F.; Misra, R. N.; Withers, G. P.; Hudrlik, A. M.; Rona, R. J.; Arcoleo, J. P. Tetrahedron Lett. 1976, 1453-1456.
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Rona, R.J.5
Arcoleo, J.P.6
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(c) Obayashi, M.; Utimoto, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1979, 52, 2646-2652.
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(d) Okamoto, S.; Shimazaki, T.; Kobayashi, Y.; Sato, F. Tetrahedron Lett. 1987, 28, 2033-2036.
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Okamoto, S.1
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Sato, F.4
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39
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0000586410
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Many examples including refs 2b, 6b, 6d, 7g, 12b, 12c, and the following: (a) Hudrlik, P. F.; Arcoleo, J. P.; Schwartz, R. H.; Misra, R. N.; Rona, R. J. Tetrahedron Lett. 1977, 591-594. (b) Obayashi, M.; Utimoto, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1979, 52, 1760-1764. (c) Berti, G.; Canedoli, S.; Crotti, P.; Macchia, F. J. Chem. Soc., Perkin Trans. 1 1984, 1183-1188. (d) Burke, S. D.; Piscopio, A. D.; Kort, M. E.; Matulenko, M. A.; Parker, M. H.; Armistead, D. M.; Shankaran, K. J. Org. Chem. 1994, 59, 332-347.
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Hudrlik, P.F.1
Arcoleo, J.P.2
Schwartz, R.H.3
Misra, R.N.4
Rona, R.J.5
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40
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0000223987
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Many examples including refs 2b, 6b, 6d, 7g, 12b, 12c, and the following: (a) Hudrlik, P. F.; Arcoleo, J. P.; Schwartz, R. H.; Misra, R. N.; Rona, R. J. Tetrahedron Lett. 1977, 591-594. (b) Obayashi, M.; Utimoto, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1979, 52, 1760-1764. (c) Berti, G.; Canedoli, S.; Crotti, P.; Macchia, F. J. Chem. Soc., Perkin Trans. 1 1984, 1183-1188. (d) Burke, S. D.; Piscopio, A. D.; Kort, M. E.; Matulenko, M. A.; Parker, M. H.; Armistead, D. M.; Shankaran, K. J. Org. Chem. 1994, 59, 332-347.
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(1979)
Bull. Chem. Soc. Jpn.
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Obayashi, M.1
Utimoto, K.2
Nozaki, H.3
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41
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3643118528
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Many examples including refs 2b, 6b, 6d, 7g, 12b, 12c, and the following: (a) Hudrlik, P. F.; Arcoleo, J. P.; Schwartz, R. H.; Misra, R. N.; Rona, R. J. Tetrahedron Lett. 1977, 591-594. (b) Obayashi, M.; Utimoto, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1979, 52, 1760-1764. (c) Berti, G.; Canedoli, S.; Crotti, P.; Macchia, F. J. Chem. Soc., Perkin Trans. 1 1984, 1183-1188. (d) Burke, S. D.; Piscopio, A. D.; Kort, M. E.; Matulenko, M. A.; Parker, M. H.; Armistead, D. M.; Shankaran, K. J. Org. Chem. 1994, 59, 332-347.
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J. Chem. Soc., Perkin Trans. 1
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Berti, G.1
Canedoli, S.2
Crotti, P.3
Macchia, F.4
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42
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0028213040
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Many examples including refs 2b, 6b, 6d, 7g, 12b, 12c, and the following: (a) Hudrlik, P. F.; Arcoleo, J. P.; Schwartz, R. H.; Misra, R. N.; Rona, R. J. Tetrahedron Lett. 1977, 591-594. (b) Obayashi, M.; Utimoto, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1979, 52, 1760-1764. (c) Berti, G.; Canedoli, S.; Crotti, P.; Macchia, F. J. Chem. Soc., Perkin Trans. 1 1984, 1183-1188. (d) Burke, S. D.; Piscopio, A. D.; Kort, M. E.; Matulenko, M. A.; Parker, M. H.; Armistead, D. M.; Shankaran, K. J. Org. Chem. 1994, 59, 332-347.
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J. Org. Chem.
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Burke, S.D.1
Piscopio, A.D.2
Kort, M.E.3
Matulenko, M.A.4
Parker, M.H.5
Armistead, D.M.6
Shankaran, K.7
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44
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0000825075
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Burford, C.; Cooke, F.; Roy, G.; Magnus, P. Tetrahedron 1983, 39, 867-876.
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Burford, C.1
Cooke, F.2
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Magnus, P.4
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45
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0001103315
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Many examples including refs 2b, 4b, 6b, 6d, 13a, and the following: (a) Ishikawa, M.; Nakagawa, K.; Katayama, S.; Kumada, M. J. Am. Chem. Soc. 1981, 103, 4170-4174. (b) Hudrlik, P. F.; Hudrlik, A. M.; Kulkarni, A. K. J. Am. Chem. Soc. 1982, 104, 6809-6811. (c) Hudrlik, P. F.; Holmes, P. E.; Hudrlik, A. M. Tetrahedron Lett. 1988, 29, 6395-6398.
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Ishikawa, M.1
Nakagawa, K.2
Katayama, S.3
Kumada, M.4
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46
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33845554964
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Many examples including refs 2b, 4b, 6b, 6d, 13a, and the following: (a) Ishikawa, M.; Nakagawa, K.; Katayama, S.; Kumada, M. J. Am. Chem. Soc. 1981, 103, 4170-4174. (b) Hudrlik, P. F.; Hudrlik, A. M.; Kulkarni, A. K. J. Am. Chem. Soc. 1982, 104, 6809-6811. (c) Hudrlik, P. F.; Holmes, P. E.; Hudrlik, A. M. Tetrahedron Lett. 1988, 29, 6395-6398.
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J. Am. Chem. Soc.
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Hudrlik, P.F.1
Hudrlik, A.M.2
Kulkarni, A.K.3
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47
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0000793399
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Many examples including refs 2b, 4b, 6b, 6d, 13a, and the following: (a) Ishikawa, M.; Nakagawa, K.; Katayama, S.; Kumada, M. J. Am. Chem. Soc. 1981, 103, 4170-4174. (b) Hudrlik, P. F.; Hudrlik, A. M.; Kulkarni, A. K. J. Am. Chem. Soc. 1982, 104, 6809-6811. (c) Hudrlik, P. F.; Holmes, P. E.; Hudrlik, A. M. Tetrahedron Lett. 1988, 29, 6395-6398.
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(1988)
Tetrahedron Lett.
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Hudrlik, P.F.1
Holmes, P.E.2
Hudrlik, A.M.3
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48
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0006473488
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(a) Tomoda, S.; Matsumoto, Y.; Takeuchi, Y.; Nomura, Y. Bull. Chem. Soc. Jpn. 1986, 59, 3283-3284.
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(b) Tomoda, S.; Matsumoto, Y.; Takeuchi, Y.; Nomura, Y. Chem. Lett. 1986, 1193-1196.
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(b) Okamoto, S.; Yoshino, T.; Tsujiyama, H.; Sato, F. Tetrahedron Lett. 1991, 32, 5793-5796.
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Okamoto, S.1
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55
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3042798830
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β-Opening has been observed in some cases, particularly where steric factors have been important: refs 1, 7k, 8c, 18c and (a) Jankowski, P.; Wicha, J. J. Chem. Soc. D 1992, 802-803. (b) Eisch, J. J.; Chiu, C. S. Heteroat. Chem. 1994, 5, 265-274. (c) Lipshutz, B. H.; Lindsley, C.; Susfalk, R.; Gross, T. Tetrahedron Lett. 1994, 35, 8999-9002. (d) Horiuchi, Y.; Taniguchi, M.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1995, 36, 5353-5356. (e) Adiwidjaja, G.; Flörke, H.; Kirschning, A.; Schaumann, E. Tetrahedron Lett. 1995, 36, 8771-8774.
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Jankowski, P.1
Wicha, J.2
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56
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84987592386
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β-Opening has been observed in some cases, particularly where steric factors have been important: refs 1, 7k, 8c, 18c and (a) Jankowski, P.; Wicha, J. J. Chem. Soc. D 1992, 802-803. (b) Eisch, J. J.; Chiu, C. S. Heteroat. Chem. 1994, 5, 265-274. (c) Lipshutz, B. H.; Lindsley, C.; Susfalk, R.; Gross, T. Tetrahedron Lett. 1994, 35, 8999-9002. (d) Horiuchi, Y.; Taniguchi, M.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1995, 36, 5353-5356. (e) Adiwidjaja, G.; Flörke, H.; Kirschning, A.; Schaumann, E. Tetrahedron Lett. 1995, 36, 8771-8774.
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Chiu, C.S.2
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7k In these cases, the isolated product was from direct epoxide opening; the possibility of rearrangement was not addressed.
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Yield calculated as if purifying all of the crude product would have resulted in the same percentage of pure product.
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