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3b-d would afford the enantiomers of monoacetate 1.
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Recently, the asymmetric reaction of the 4-cyclopentene-1,3-diol diacetate with soft nucleophiles in the presence of a palladium catalyst and a chiral ligand has been reported: (a) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016-2021. (b) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327-9343. (c) Mori, M.; Nukui, S.; Shibasaki, M. Chem. Lett. 1991, 1797-1800.
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Recently, the asymmetric reaction of the 4-cyclopentene-1,3-diol diacetate with soft nucleophiles in the presence of a palladium catalyst and a chiral ligand has been reported: (a) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016-2021. (b) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327-9343. (c) Mori, M.; Nukui, S.; Shibasaki, M. Chem. Lett. 1991, 1797-1800.
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Recently, the asymmetric reaction of the 4-cyclopentene-1,3-diol diacetate with soft nucleophiles in the presence of a palladium catalyst and a chiral ligand has been reported: (a) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016-2021. (b) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327-9343. (c) Mori, M.; Nukui, S.; Shibasaki, M. Chem. Lett. 1991, 1797-1800.
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10b-d However, the methods suffer from a chemical instability of 12.
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The aldol products and the coupling constants measured are as follows: 43a, 8.7 Hz; 46a, 3 Hz; 43b, 9.3 Hz; 46b, ca. 3 Hz; 43c, 9.6 Hz; 46c, 3 Hz; 43d, 9.0 Hz; 46d, 3 Hz; 44a, 8.4 Hz; 47a, 3 Hz; 44b, 9.0 Hz; 47b, ca. 3 Hz; 44c, 9.6 Hz; 47c, ca. 3 Hz. However, coupling constants of 45a-c and 48a-c could not be determined because of overlap of the diagnostic signals.
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100
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note
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3N produced iii and iv with different ratios depending on the conditions employed. Other amines did not improve the result.
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4NF in THF resulted in production of several unidentified compounds.
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