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A small amount of THF (0.3 equiv) must be added to suppress the formation of side product to afford 78% yield with an α to γ ratio of 70/30. This is because the corresponding α-adduct undergoes an oxonium-ene cyclization with aldehyde immediately once the α-adduct was synthesized. For reference, see: Loh, T. P.; Hu, Q. Y.; Tan, K. T.; Cheng, H. S. Org. Lett. 2001, 3, 2669.
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We also tried to add 6 equiv of water to the reaction; yet, a lower yield was obtained. For example, reaction of hexanal aldehyde with cinnamyl bromide in 6 equiv of water for 24 h afforded only 22% yield with no change in regioselectivity.
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50
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note
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The zinc powder was used directly from the bottle purchased from Merck.
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With hindered ketones such as di-tert-butyl ketone or di-iso-propyl ketone, the α-adducts might be formed from fission of the C-C bond or directly from the ketone and the crotyl Grignard via a four-center transition state, see: Benkeser, R. A.; Siklosi, M. P.; Mozdzen, E. C. J. Am. Chem. Soc. 1978, 100, 2134.
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Process which converts readily available kinetic products to their less readily accessible thermodynamic isomers, see: (a) Barbot, F.; Miginiac, P. Tetrahedron Lett. 1975, 3829. (b) Gedye, R. N.; Arora, P.; Khalil, A. H. Can. J. Chem. 1975, 53, 1943. (c) Tatsuta, K.; Tamura, T.; Mase, T. Tetrahedron Lett. 1999, 40, 1925. For an example of a γ-adduct rearranging to its α-adduct, see: (d) Hong, B. C.; Hong, J. H.; Tsai, Y. C. Angew. Chem., Int. Ed. 1998, 37, 468.
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An alternative mechanism for the formation of α-adduct via ah an intramolecular [1,3]-sigmatropic rearrangement, contradicting the results from the crossover experiment, which points towards an intermolecular rearrangement. For reference, see: Wilson, S. T. Org. React. 1993, 43, 93.
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We found that InBr can catalyze the rearrangement of γ-adducts to their corresponding α-adducts too.
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3 to the γ-adduct in various solvents, including 6 equiv of water, DMF, and THF. Results revealed that after 72 h at room temperature, only the mixture in 6 equiv of water showed signs of rearrangement (γ: α ≈ 78:22), while those in DMF and THF showed no progress. In fact, when 12 equiv of water was used, no rearrangement was observed as well.
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