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23744504437
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The starting acyl cyanide was prepared according to
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The starting acyl cyanide was prepared according to: Jung M. E., Min S.-J. J. Am. Chem. Soc.: 2005; 127 10834
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37
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84906790395
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In aldol adducts where the chiral carbon between the carbonyl group and the hydroxy group contains a bulky substituent, the syn isomer shows a larger coupling constant than the anti isomer, e.g. see
-
In aldol adducts where the chiral carbon between the carbonyl group and the hydroxy group contains a bulky substituent, the syn isomer shows a larger coupling constant than the anti isomer, e.g., see: Heng K. K., Simpson J., Smith R. A. J, Robinson W. T. J. Org. Chem.: 1981; 46 2032
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Kitamura M., Nakano K., Miki T., Okada M., Noyori R. J. Am. Chem. Soc.: 2001; 123 8939
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40
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84906790837
-
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Our stereochemical assignment is in full agreement with the X-ray structure depicted in ref. 15. For other examples of aldol reactions of sterically congested ester enolates with aldehydes, see
-
Our stereochemical assignment is in full agreement with the X-ray structure depicted in ref. 15. For other examples of aldol reactions of sterically congested ester enolates with aldehydes, see
-
-
-
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41
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0034615548
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Indium enolates
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Indium enolates: Hirashita T., Kinoshita K., Yamamura H., Kawai M., Araki S. J. Chem. Soc., Perkin Trans. 1: 2000; 825
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0002857938
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Zinc enolates
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Zinc enolates: Wei C.-Q, Zhao G., Jiang X.-R, Ding Y. J. Chem. Soc., Perkin Trans. 1: 1999; 3531
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45
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0001015873
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® as a base in alkylation reactions of sensitive aldol adducts was reported in
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® as a base in alkylation reactions of sensitive aldol adducts was reported in: Diem M. J., Burow D. F., Fry J. L. J. Org. Chem.: 1977; 42 1801
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0020054831
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® gave a maximum yield of 60%, e.g. see
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47
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0000488346
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MeI/NaH gave a complex product mixture, see
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48
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0026721571
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85022455957
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84906790209
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In a related RCM reaction with the Grubbs II catalyst (Scheme 6), we also observed acceleration exerted by a geminal dimethyl arrangement (Feidt, E. unpublished results). For the RCM of 1,9-decadiene into cyclooctene, see
-
In a related RCM reaction with the Grubbs II catalyst (Scheme 6), we also observed acceleration exerted by a geminal dimethyl arrangement (Feidt, E. unpublished results). For the RCM of 1,9-decadiene into cyclooctene, see
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67
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78149440897
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72
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84906791514
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3.
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14b The final refinement resulted in: R 1 = 0.036. Crystallographic data for this structure have been deposited with the Cambridge Crystallographic Data Centre, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. Copies of the data can be obtained free of charge on quoting the deposition number CCDC 990861 (www.ccdc.cam.ac.uk/data-request/cif).
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80053539485
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80
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84906790210
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For additional details, see: US Patent 3524884; Chem. Abstr. 1970, 73, 87533.
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Kretschmar, H.C.1
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0009896481
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For an analogous reaction giving a bicyclo[3.2.1]octan-8-one skeleton, see
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For an analogous reaction giving a bicyclo[3.2.1]octan-8-one skeleton, see: Nelsen S. F., Kapp D. L. J. Am. Chem. Soc.: 1986; 108 1265
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0345695763
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2O, 9:1, reflux, 3 d). The acid chloride 15 was prepared according to ref. 17f.
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2O, 9:1, reflux, 3 d). The acid chloride 15 was prepared according to ref. 17f.
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19944370115
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