The Use of Lewis Acids in Radical Chemistry. Chelation-Controlled Radical Reductions of Substituted α-Bromo-β-alkoxy Esters and Chelation-Controlled Radical Addition Reactions

Journal of Organic Chemistry

Volumn 63, Issue 19, 1998, Pages 6554-6565

  Guindon, Yvan ^a,b   Rancourt, J ^c  

^a CLIN RESEARCH INSTITUTE OF MONTREAL   (Canada)

^b UNIVERSITÉ DE MONTRÉAL   (Canada)

^c BOEHRINGER INGELHEIM CANADA LTD   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000934736     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980636x     Document Type: Article

References (94)

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60. The unsaturated esters were either purchased or prepared from the corresponding acids, which were commercially available. Unsaturated esters 4 and 5 were prepared from an aldol condensation (LDA, THF, -78°C then PhCHO) followed by dehydration (MsCl, pyridine then DBU, toluene).
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67. A similar observation has been made in the chelation-controlled allylation of secondary α-iodoesters; see ref 7b.
68. To ensure that the radical process was quenched at the same temperature at which the reaction was conducted, a radical inhibitor, m-dinitrobenzene (m-DNB), was added to the reaction mixture prior to workup.
69. The relative configuration of the reduced products was established by correlation of NMR chemical shifts. In all cases, the methyl group adjacent to the ester function resonated slightly downfield for the syn compounds relative to the corresponding resonance of the anti isomers. The original NMR reference assignments were verified by X-ray crystallographic structures; see ref 4d.
70. For purposes of comparison, these reactions were all performed at 0°C since the tert-butyl substrate 31 was insoluble at lower temperatures. Substrates 16, 26, and 28 gave higher ratios at -78°C.
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75. An increase in the radical based polymerization rate has been observed in the presence of a Lewis acid: (a) Imoto, M.; Otsu, T.; Harada, Y. Makromol. Chem. 1963, 65, 180. (b) Yabumoto, S.; Ishii, K.; Arita, K. J. Polym, Sci. A-1, 1969, 7, 1577. (c) Inoue, H.; Otsu, T. Die Makromol. Chem. 1972, 153, 21. See also ref 29.
76. An increase in the radical based polymerization rate has been observed in the presence of a Lewis acid: (a) Imoto, M.; Otsu, T.; Harada, Y. Makromol. Chem. 1963, 65, 180. (b) Yabumoto, S.; Ishii, K.; Arita, K. J. Polym, Sci. A-1, 1969, 7, 1577. (c) Inoue, H.; Otsu, T. Die Makromol. Chem. 1972, 153, 21. See also ref 29.
77. 6e
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81. (d) Kuvila, H. G. Synthesis 1970, 499.
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83. (b) Blackburn, E. V.; Tanner, D. D. J. Am. Chem. Soc. 1980, 102, 692. See also refs 3a-d.
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85. (b) Xiao, X.; Pan, H.-Q.; Dolbier, W. R., Jr. J. Am. Chem. Soc. 1994, 116, 4521.
86. Oxygen atoms of hindered silyl ethers are known to be less efficient in complexation with Lewis acids; see Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1992, 114, 1778 and references therein.
87. 2 is present in excess relative to the substrate.
88. (a) See refs 4c and 4e.
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