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12244268637
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note
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10b however, the enantiomeric purity was decreased when a long-chain alkyl group was present.
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-
-
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27
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0000883846
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19F NMR analysis of the Mosher ester formed by the reaction of the alcohol with -(+)-α-methoxy-α-(trifluoromethyl)phenylacetic acid (MTPA) chloride in the presence of DMAP: Guivisdalsky, P. N.; Bittman, R. J. Org. Chem. 1989, 54, 4637-4642.
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0000794537
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Alpine-Borane is a trademark of Aldrich Chemical Co. For the preparation of -Alpine-Borane and its use in the asymmetric reduction of 1-octyn-3-one, see: (a) Midland, M. M.; Graham, R. S. Org. Synth. 1985, 63, 57-65. (b) For a review of asymmetric reduction of propargyl ketones with Alpine-Borane, see: Midland, M. M.; Tramontano, A.; Kazubski, A.; Graham, R. S.; Tsai, D. J. S.; Cardin, D. B. Tetrahedron 1984, 40, 1371-1380.
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Alpine-Borane is a trademark of Aldrich Chemical Co. For the preparation of -Alpine-Borane and its use in the asymmetric reduction of 1-octyn-3-one, see: (a) Midland, M. M.; Graham, R. S. Org. Synth. 1985, 63, 57-65. (b) For a review of asymmetric reduction of propargyl ketones with Alpine-Borane, see: Midland, M. M.; Tramontano, A.; Kazubski, A.; Graham, R. S.; Tsai, D. J. S.; Cardin, D. B. Tetrahedron 1984, 40, 1371-1380.
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0037020635
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For a preliminary account of the preparation of both R and S long-chain propargylic alcohols in high ee via AD reaction of α,β unsaturated esters with either AD-mix-α or AD-mix-β, see: Chun, J.; Byun, H.-S.; Bittman, R. Tetrahedron Lett. 2002, 43, 8043-8045.
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12244285661
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-
note
-
D +8.9° (c 1.0, MeOH)).
-
-
-
-
40
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0028225954
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For the "buffered" AD reaction of allylic halides, see: Vanhessche, K. P. M.; Wang, Z.-M.; Sharpless, K. B. Tetrahedron Lett. 1994, 35, 3469-3472.
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12244285660
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note
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1H NMR spectroscopy.
-
-
-
-
45
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0023838180
-
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For examples of high anti:syn ratios in the addition of alkynyl-lithium reagents to 26 in the presence of HMPA, see: (a) Herold, P. Helv. Chim. Acta 1988, 71, 354-362. (b) Gruza, H.; Kiciak, K.; Krasinski, A.; Jurczak, J. Tetrahedron: Asymmetry 1997, 8, 2627-2631.
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Herold, P.1
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For examples of high anti:syn ratios in the addition of alkynyl-lithium reagents to 26 in the presence of HMPA, see: (a) Herold, P. Helv. Chim. Acta 1988, 71, 354-362. (b) Gruza, H.; Kiciak, K.; Krasinski, A.; Jurczak, J. Tetrahedron: Asymmetry 1997, 8, 2627-2631.
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0141712450
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Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768-2771.
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49
-
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12244271464
-
-
note
-
The 1,3-oxazolidine carbamate system exists as a pair of rotamers, the interconversion of which is enhanced at high temperature; therefore, proton NMR spectra were recorded at 70 °C.
-
-
-
-
50
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12244251420
-
-
note
-
13C NMR spectra appear as a pair of singlets (denoted in parentheses).
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