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To the best of our knowledge, only one example of a CM reaction involving sulfinyl amines was reported in the literature: J. C. González- Gómez, F. Foubelo, M. Yus, Synlett 2008, 2702.
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77955890608
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2, gave the CM product 4b in only 21% yield
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2, gave the CM product 4b in only 21% yield.
-
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40
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70549113223
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A recent study of the intramolecular aza-Michael reaction under basic conditions showed a similar influence of the base in the selectivity: C. Enkisch, C. Schneider, Eur. J. Org. Chem. 2009, 5549.
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77955903908
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Although under basic conditions the formation of piperidine derivatives were more favorable with p-tolyl sulfinyl amines, the corresponding CM reaction to obtain the Michael acceptor took place in only 5% yield, and we decided to use the tert-butyl sulfinyl amine in the process
-
Although under basic conditions the formation of piperidine derivatives were more favorable with p-tolyl sulfinyl amines, the corresponding CM reaction to obtain the Michael acceptor took place in only 5% yield, and we decided to use the tert-butyl sulfinyl amine in the process.
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43
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34249785081
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We have previously described in a preliminary communication the synergistic effect of second-generation Hoveyda-Grubbs catalyst with boron trifluoride in an analogous tandem process with carbamates as the source of the nucleophilic nitrogen
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We have previously described in a preliminary communication the synergistic effect of second-generation Hoveyda-Grubbs catalyst with boron trifluoride in an analogous tandem process with carbamates as the source of the nucleophilic nitrogen: S. Fustero, D. Jimémnez, M. Sánchez- Roselló, C. del Pozo, J. Am. Chem. Soc. 2007, 129, 6700.
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77955888387
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2 at -78°C furnished the desired diastereoisomer although in a modest 30% yield
-
2 at -78°C furnished the desired diastereoisomer although in a modest 30% yield.
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