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1
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0343518211
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Encyclopedia of Reagents for Organic Synthesis Ed.; John Wiley and Sons: New York, and pp. 3166-3172, respectively
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Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley and Sons: New York, pp. 3096-3104 and pp. 3166-3172, respectively.
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Paquette, L.A.1
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3
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0001113382
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and
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Corey, E. J.; Gross, A. W. Tetrahedron Lett. 1984, 25, 495 and Org. Synth. Coll. Vol. VIII, 93.
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Org. Synth. Coll.
, vol.8
, pp. 93
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4
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0028216123
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Lithium tetramethylpiperidide has also been found to produce E-silyl ketene acetals via the corresponding transoid enolates provided that a bulky silylating agent is used, e.g. triisopropyl silyl chloride; see Hattori, K.; Yamamoto, H. Tetrahedron 1994, 50, 3099.
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Lithium tetramethylpiperidide has also been found to produce E-silyl ketene acetals via the corresponding transoid enolates provided that a bulky silylating agent is used, e.g. triisopropyl silyl chloride; see
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(1994)
Tetrahedron
, vol.50
, pp. 3099
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Hattori, K.1
Yamamoto, H.2
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6
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0343954045
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Blount, J. F.; Gutiérrez, A.; Mislow, K. J. Org. Chem. 1982, 47, 4359.
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(1982)
Org. Chem.
, vol.47
, pp. 4359
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Blount, J.F.1
Gutiérrez, A.2
Mislow, K.J.3
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7
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0343518210
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3): δ 7.65 (d, J=7.4 Hz, 6H), 7.23 (t, J=7.4 Hz, 6H), 7.13 (t, J=7.4 Hz, 3H), 0.81 (s, 9H) ppm
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3): δ 7.65 (d, J=7.4 Hz, 6H), 7.23 (t, J=7.4 Hz, 6H), 7.13 (t, J=7.4 Hz, 3H), 0.81 (s, 9H) ppm.
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8
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0343518209
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Preparation of ketene acetals using lithium t-butyltritylamide. (Typical procedure): t-butyltritylamine (1.20 g, 3.81 mmol) was dissolved in 3 mL THF, and the solution was dried over 4 Å molecular sieves and transferred to the reaction flask. After cooling to 0°C, n-BuLi (2.34 mL, 3.81 mmol) was added dropwise and the reaction mixture was stirred at 0°C for 45 min. The resulting solution of 2 was cooled to -78°C and TMSCl (0.73 mL, 5.81 mmol) was added dropwise. p-Methoxyphenoxyacetic acid t-butyl ester (758 mg, 3.18 mmol) was dissolved in 2 mL THF and the solution was dried over 4 Å molecular sieves and transferred dropwise after cooling to -78°C to the reaction mixture. The reaction mixture was stirred at -78°C for 1.5 h and concentrated to remove solvent and excess TMSCl. The crude product was dissolved in dry pentane and LiCl was removed by filtration through a Teflon filter. The pentane solution was concentrated, cooled to -20°C and then seeded
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6) δ 6.95 (d, J=9.0 Hz, 2H), 6.69 (d, J=9.0 Hz, 2H), 5.89 (s, 1H), 3.26 (s, 3H), 1.28 (s, 9H), 0.28 (s, 9H) ppm.
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9
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0343082116
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Approximate prices of precursor materials (Aldrich 1999): trityl chloride, 100 g, $ 22.45; t-butylamine, 100 mL, $ 23.55
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Approximate prices of precursor materials (Aldrich 1999): trityl chloride, 100 g, $ 22.45; t-butylamine, 100 mL, $ 23.55.
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10
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0343518208
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Detailed X-ray crystallographic data for 1, 6 and 7 are available from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ, UK
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Detailed X-ray crystallographic data for 1, 6 and 7 are available from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ, UK.
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11
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0343954042
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We are grateful to Drs. Georgios Sarakinos and Axel Fischer for experimental assistance and to the National Institutes of Health and Pfizer Inc for financial assistance
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We are grateful to Drs. Georgios Sarakinos and Axel Fischer for experimental assistance and to the National Institutes of Health and Pfizer Inc for financial assistance.
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