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The literature contains very few reports of stoichiometric crossover transfer hydrogenation reactions between alcohols and alkenes. A few examples of crossover transfer hydrogenation using a small excess of alkene acceptor have been reported. See for example: M. E. Krafft, B. Zorc, J. Org. Chem. 1986, 51, 5482.
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There are numerous reports of tandem oxidation-olefination reactions (2 of the 3 steps involved in our domino reaction sequence). See for example: a) L. Blackburn, R. J. K. Taylor, Synlett 2002, 215;
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33749429245
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note
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Control experiments in the presence of excess alcohol exhibited no hydrogenolysis of the benzyl ester.
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49
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33749449542
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note
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The ultimate fate of carbon monoxide is unknown. Iridium carbonyl complexes are stable species thus it is plausible that this step represents a catalyst termination event.
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note
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3-methyl-2-buten-1-ol (not shown) afforded a complex reaction mixture from which none of the desired product could be isolated.
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65
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33749432218
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note
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Reactions with the cyano ylide 19 yielded mixtures of E/Z α,β-unsaturated nitriles, even under the thermodynamic conditions.
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note
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This particular substrate proved troublesome to isolate both because of its volatility and the tendency for it to be destroyed under the oxidative workup conditions; identification of the product was therefore achieved by hydrogenation of the alkene present in the alkene/alkane mixture.
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72
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33749427277
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note
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Under the domino reaction conditions the olefination reaction is rapid.
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74
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0001215094
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