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4544334973
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note
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Novel acylating reagents (3a,b) were prepared by the addition of the monoalkyl maleate 7 to ethoxyacetylene in a similar way to the preparation of the related ethoxyvinyl esters. Although initial studies were carried out with purified 3 to examine diverse reaction conditions, a more practical one-pot method with crude 3 also gave a similar result, as shown in Table 3.
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25
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37049070301
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The related intramolecular Diels-Alder reactions have been carried out at high temperatures, such as 120-150°C, in aromatic solvents or with microwave irradiation; however, the yields of the products were moderate. We found that the reaction of 4a in polar solvents gradually proceeded even at room temperature to give almost quantitative yields of 5a. a) M. J. Batchelor, J. M. Mellor, J. Chem. Soc. Perkin Trans. 1 1989, 985-995;
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Mellor, J.M.2
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4544280030
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note
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Optically purity of the products was determined by HPLC analysis with a chiral column: Daicel Chiralcel OD for 2a, 4a, 5a, and 5b, Daicel Chiralpak AD-H for 5c and 5d. The absolute and relative stereochemistries of the products were determined as shown in the schemes (see the Supporting Information for further details).
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4544293291
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note
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The reactivity of 1c was confirmed by the complete racemization of 1-phenylethanol (99% ee) within 1 h at room temperature according to the reported method.
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4544229061
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note
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The catalyst if was also highly effective for the racemization of optically pure 3-hydroxy-1-phenylbut-1-ene, for which the use of 1d or le was reported to generate the corresponding ketones in 18-25% combined yields. (see the Supporting Information for further details).
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