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In contrast, the catalyst EtAlCl2 (20 mol %) gives the adducts of ethyl acrylate and 1- and 2-methylcyclopentadiene in a 7:3 ratio; it thus favors the formation of the product derived from 2-methylcyclopentadiene.
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J. N. Payette, H. Yamamoto, J. Am. Chem. Soc. 2007, 129, 9536-9537. In contrast, the catalyst EtAlCl2 (20 mol %) gives the adducts of ethyl acrylate and 1- and 2-methylcyclopentadiene in a 7:3 ratio; it thus favors the formation of the product derived from 2-methylcyclopentadiene.
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For oxazaborolidinium activation of methyl aryl ketones, see:
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For oxazaborolidinium activation of methyl aryl ketones, see: a) D. H. Ryu, E. J. Corey, J. Am. Chem. Soc. 2005, 127, 5384-5387;
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For a discussion of the role of hydrogen bonding in enantioselective Lewis acid catalysis, see
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For a discussion of the role of hydrogen bonding in enantioselective Lewis acid catalysis, see : b) E. J. Corey, T. W Lee, Chem. Commun. 2001, 1321-1329.
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58149176972
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DFT studies on oxazaborolidinium catalysis suggest that hydrogen bonding between the catalyst and the substrate may not always occur
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a) DFT studies on oxazaborolidinium catalysis suggest that hydrogen bonding between the catalyst and the substrate may not always occur: M. N. Paddon-Row, L. C. H. Kwan, A. C. Willis, M. S. Sherburn, Angew. Chem. 2008, 120, 7121-7125;
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For experimental support for these findings, see
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For experimental support for these findings, see: b) E. P. Balskus, E. N. Jacobsen, Science 2007, 317, 1736-1740.
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0001015795
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For a discussion of the Corey-Bakshi-Shibata (CBS) reduction of alkynyl ketones, see
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70349954897
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The X-ray crystal structure does not indicate the presence of a hydrogen bond between O2-H and O3.
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The X-ray crystal structure does not indicate the presence of a hydrogen bond between O2-H and O3.
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29
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70349964539
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Acetylenic esters were screened as dienophiles with various cyclic and acyclic dienes. However, presumably as a result of their lower reactivity, no product was detected.
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Acetylenic esters were screened as dienophiles with various cyclic and acyclic dienes. However, presumably as a result of their lower reactivity, no product was detected.
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