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1
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For selected reviews of enantioselective carbonyl allylation, see: a
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For selected reviews of enantioselective carbonyl allylation, see: (a) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763.
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(b) Yu, C.-M.; Youn, J.; Jung, H.-K. Bull. Korean Chem. Soc. 2006, 27, 463.
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37049095180
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For enantioselective aldehyde alkoxyallylation employing alkoxy-substituted allylboron reagents, see: a
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For enantioselective aldehyde alkoxyallylation employing alkoxy-substituted allylboron reagents, see: (a) Wuts, P. G. M.; Bigelow, S. S. J. Chem. Soc., Chem. Commun. 1984, 736.
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(b) Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1988, 110, 1535.
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0032510085
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For aldehyde alkoxyallylation employing alkoxy-substituted allylaluminum reagents, see
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For aldehyde alkoxyallylation employing alkoxy-substituted allylaluminum reagents, see: Chika, J.-i.; Takei, H. Tetrahedron Lett. 1998, 39, 605.
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Chika, J.-I.1
Takei, H.2
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0001359587
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For aldehyde alkoxyallylation employing alkoxy-substituted allyltitanium reagents, see: Hafner, A, Duthaler, R. O, Marti, R, Rihs, G, Rothe-Streit, P, Schwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321. To our knowledge, Duthaler's chirally modified allyltitanium reagent is unique in its ability to promote highly stereocontrolled direct anti-alkoxyallylation of aldehydes. For a highly enantioselective indirect method, see ref 8
-
For aldehyde alkoxyallylation employing alkoxy-substituted allyltitanium reagents, see: Hafner, A.; Duthaler, R. O.; Marti, R.; Rihs, G.; Rothe-Streit, P.; Schwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321. To our knowledge, Duthaler's chirally modified allyltitanium reagent is unique in its ability to promote highly stereocontrolled "direct" anti-alkoxyallylation of aldehydes. For a highly enantioselective indirect method, see ref 8.
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-
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11
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0000544750
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For aldehyde alkoxyallylation employing alkoxy-substituted allylindium reagents, see: a
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For aldehyde alkoxyallylation employing alkoxy-substituted allylindium reagents, see: (a) Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920.
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Marshall, J.A.1
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0001700614
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For aldehyde alkoxyallylation employing alkoxy-substituted allyltin reagents, see: a
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For aldehyde alkoxyallylation employing alkoxy-substituted allyltin reagents, see: (a) Marshall, J. A.; Gung, W. Y. Tetrahedron Lett. 1989, 30, 2183.
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Marshall, J.A.1
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(c) Yamamoto, Y.; Kobayashi, K.; Okano, H.; Kadota, I. J. Org. Chem. 1992, 57, 7003.
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Yamamoto, Y.1
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0001123065
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f Reference 5 cited above
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(e) Kadota, I.; Kobayashi, K.; Okano, H.; Asao, N.; Yamamoto, Y. Bull. Soc. Chim. Fr. 1995, 132, 615. (f) Reference 5 cited above.
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Kadota, I.1
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0001170148
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2 = Si, see: Tamao, K.; Nakajo, E.; Ito, Y. J. Org. Chem. 1987, 52, 957.
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2 = Si, see: Tamao, K.; Nakajo, E.; Ito, Y. J. Org. Chem. 1987, 52, 957.
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19
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0000472811
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2 = B, see: Brown, H. C.; Narla, G. J. Org. Chem. 1995, 60, 4686.
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2 = B, see: Brown, H. C.; Narla, G. J. Org. Chem. 1995, 60, 4686.
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20
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0025687659
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2 = Si, see: (a) Roush, W. R.; Grover, P. T.; Lin, X. Tetrahedron Lett. 1990, 31, 7563.
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2 = Si, see: (a) Roush, W. R.; Grover, P. T.; Lin, X. Tetrahedron Lett. 1990, 31, 7563.
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24
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(e) Yamamoto, Y.; Miyairi, T.; Ohmura, T.; Miyaura, N. J. Org. Chem. 1999, 64, 296.
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(f) Roush, W. R.; Pinchuk, A. N.; Micalizio, G. C. Tetrahedron Lett. 2000, 41, 9413.
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Roush, W.R.1
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27
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0028960210
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Direct metallation of allyl ethers is Z-selective as a result of chelation. Hence, access to E-configured alkoxy-substituted allylmetal reagents and the resulting anti-1,2-diols has been problematic. For a more detailed discussion, see: Moriya, T.; Suzuki, A.; Miyaura, N. Tetrahedron Lett. 1995, 36, 1887, and refs 8 and 9c.
-
Direct metallation of allyl ethers is Z-selective as a result of chelation. Hence, access to E-configured alkoxy-substituted allylmetal reagents and the resulting anti-1,2-diols has been problematic. For a more detailed discussion, see: Moriya, T.; Suzuki, A.; Miyaura, N. Tetrahedron Lett. 1995, 36, 1887, and refs 8 and 9c.
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28
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0000016656
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Upon exposure of cis,trans-2,3-hexadiene to conditions for osmium-catalyzed asymmetric dihydroxylation, the trans olefin reacts preferentially to provide the syn diol. See: Xu, D.; Crispino, G. A.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7570.
-
Upon exposure of cis,trans-2,3-hexadiene to conditions for osmium-catalyzed asymmetric dihydroxylation, the trans olefin reacts preferentially to provide the syn diol. See: Xu, D.; Crispino, G. A.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7570.
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29
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77249140552
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As described in ref 14e, preactivation refers to the degree of separation between a reagent or reactant and the parent feedstocks
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As described in ref 14e, preactivation refers to the degree of separation between a reagent or reactant and the parent feedstock(s).
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30
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0038639779
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This process employs 3-chloropropenyl pivalate as the allyl donor, and only modest levels diastereo- and enantioselectivity are observed. For catalytic enantioselective aldehyde alkoxyallylation via Nozaki-Hiyama coupling, see
-
For catalytic enantioselective aldehyde alkoxyallylation via Nozaki-Hiyama coupling, see: Lombardo, M.; Licciulli, S.; Morganti, S.; Trombini, C. Chem. Commun. 2003, 1762. This process employs 3-chloropropenyl pivalate as the allyl donor, and only modest levels diastereo- and enantioselectivity are observed.
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Chem. Commun
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Lombardo, M.1
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33846995439
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For selected reviews of C-C bond-forming hydrogenation and transfer hydrogenation, see: a
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For selected reviews of C-C bond-forming hydrogenation and transfer hydrogenation, see: (a) Ngai, M.-Y.; Kong, J. R.; Krische, M. J. J. Org. Chem. 2007, 72, 1063.
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36
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43949139260
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For enantioselective carbonyl allylation, crotylation, and tert-prenylation via iridium-catalyzed C-C bond-forming transfer hydrogenation, see: (a) Kim, I. S.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6340.
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For enantioselective carbonyl allylation, crotylation, and tert-prenylation via iridium-catalyzed C-C bond-forming transfer hydrogenation, see: (a) Kim, I. S.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6340.
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(b) Kim, I. S.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14891.
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(c) Kim, I. S.; Han, S. B.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 2514.
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