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0001290261
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Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
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(c) Snider, B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 527-561.
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(d) Houston, T. A.; Tanaka, Y.; Koreeda, M. J. Org. Chem. 1993, 58, 4287-4292.
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(e) Aggarwal, V. K.; Vennall, G. P.; Davey, P. N.; Newman, C. Tetrahedron Lett. 1998, 39, 1997-2000.
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Aggarwal, V.K.1
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0036354877
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(g) Loh, T. P.; Feng, L. C.; Yang, J. Y. Synthesis 2002, 7, 937-940.
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Loh, T.P.1
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Yang, J.Y.3
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13
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0008297107
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One isolated example of a carbonyl-ene reaction of an aromatic aldehyde and a monosubstituted alkene has been described (yield not reported): Epifani, E.; Florio, S.; Ingrosso, G. Tetrahedron 1988, 44, 5869-5877.
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Epifani, E.1
Florio, S.2
Ingrosso, G.3
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14
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0001673303
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For intramolecular examples, see: (a) Andersen, N. H.; Hadley, S. W.; Kelly, J. D.; Bacon, E. R. J. Org. Chem. 1985, 50, 4144-4151.
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Andersen, N.H.1
Hadley, S.W.2
Kelly, J.D.3
Bacon, E.R.4
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15
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13244255481
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(b) Fujita, M.; Shindo, M.; Shishido, K. Tetrahedron Lett. 2005, 46, 1269-1271.
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Fujita, M.1
Shindo, M.2
Shishido, K.3
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17
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0039896797
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Lappin, G. R., Sauer, J. D., Eds.; M. Dekker: New York
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Alpha Olefins Applications Handbook; Lappin, G. R., Sauer, J. D., Eds.; M. Dekker: New York, 1989.
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Alpha Olefins Applications Handbook
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18
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0003106821
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Ni(II)-catalyzed carbonyl-ene reactions of 1,1-disubstituted alkenes and glyoxylate esters: Mikami, K.; Aikawa, K. Org. Lett. 2002, 4, 99-101.
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Org. Lett.
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, pp. 99-101
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Mikami, K.1
Aikawa, K.2
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19
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33646460924
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note
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This selectivity has been observed in one thermal carbonyl-ene reaction (6-methyl-1,5-heptadiene and the highly electron-deficient diethyl oxomalonate, 180 °C, 24 h):
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20
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33847085044
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(a) Salomon, M. F.; Pardo, S. N.; Salomon, R. G. J. Am. Chem. Soc. 1980, 102, 2473-2475.
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Salomon, M.F.1
Pardo, S.N.2
Salomon, R.G.3
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21
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0021439255
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(b) Salomon, M. F.; Pardo, S. N.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797-3802.
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Salomon, M.F.1
Pardo, S.N.2
Salomon, R.G.3
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23
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4644370089
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See also: (a) Ogoshi, S.; Oka, M.-a.; Kurosawa, H. J. Am. Chem. Soc. 2004, 126, 11802-11803.
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Ogoshi, S.1
Oka, M.-A.2
Kurosawa, H.3
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24
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25144460599
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(b) Ogoshi, S.; Ueta, M.; Arai, T.; Kurosawa, H. J. Am. Chem. Soc. 2005, 127, 12810-12811.
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Ogoshi, S.1
Ueta, M.2
Arai, T.3
Kurosawa, H.4
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25
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33646456927
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-
note
-
See Supporting Information for details.
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-
-
-
26
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33646451827
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note
-
Aldehydes bearing one or more α-hydrogens, e.g., isobutyraldehyde, undergo competitive enolsilane formation.
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-
-
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27
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0002324898
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Review of the Sakurai reaction: Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 37, 57-575.
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(1989)
Org. React.
, vol.37
, pp. 57-575
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Fleming, I.1
Dunogues, J.2
Smithers, R.3
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28
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33646438388
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note
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Reactions of p-nitrobenzaldehyde afforded no trace of coupling product.
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-
-
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29
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33646466019
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note
-
Coupling products were not detected when methallylbenzene, cis-4-octene, and trans-4-octene were employed.
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