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(d) For an organocatalytic reaction: Juhl, K.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498-1501.
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The bulky N-mesityl substituent is critical for the high yields and enantioselectivities in NHC-catalyzed Diels-Alder reactions. The design and synthesis of this triazolium salt draws on pioneering work by Leeper, Rovis, and Enders; see (a) Teles, J. H.; Melder, J.-P.; Ebel, K.; Schneider, R.; Gehrer, E.; Harder, W.; Brode, S.; Enders, D.; Breuer, K.; Raabe, G. Helv. Chim. Acta 1996, 79, 61-83.
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33845199836
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note
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Shorter reaction times give higher diastereoselectivities. Resubjecting the diastereomerically pure cis product obtained in Table 1, entry 3 to the reaction conditions afforded a 3:1 mixture of diastereomers.
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26
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0001320447
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For the synthesis and diastereoselective elaboration of a similar product, see Evans, D. A.; Janey, J. M. Org, Lett. 2001, 3, 2125-2128.
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