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For recent reviews on ynamines and ynamides, see: (a) Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575.
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For the synthesis of ynamides using copper catalyzed amidations, see: (a) Frederick, M. O.; Mulder, J. A.; Tracey, M. R.; Hsung, R. P.; Huang, J.; Kurtz, K. C. M.; Shen, L.; Douglas, C. J. J. Am. Chem. Soc. 2003, 125, 2368.
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Also see Ref. 9a,k
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(b) Also see Ref. 9a,k.
-
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18
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0035857270
-
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For the synthesis of ynamides using an based promoted elimination Z-beta-bromo enamides, see: Wei, L.-L.; Mulder, J. A.; Xiong, H.; Zificsak, C. A.; Douglas, C. J.; Hsung, R. P. Tetrahedron 2001, 57, 459.
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Also see: Couty, S.; Barbazanges, M.; Meyer, C.; Cossy, J. Synlett 2005, 906.
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85030727896
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note
-
In addition to reviews in Ref. 1, please see papers in this special issue for a range of elegant chemistry employing electron deficient ynamines.
-
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21
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For recent reports on the chemistry of ynamides in the last 3 years, see: (a) Dunetz, J. R.; Danheiser, R. L. J. Am. Chem. Soc. 2005, 127, 5776.
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See Ref. 15
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Stereochemistry at C2 of the major isomers was assigned based on related Claisen rearrangement using allyl alcohols. See Ref. 15. Attempts to gain crystal structures failed, and isomers with moderate ratios are also difficult to separate.
-
-
-
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80
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85030736555
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note
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Allene 40 was obtained in 67% as a single isomer from the reaction of ynamide (R)-10 with chiral propargyl alcohol (S)-35.
-
-
-
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81
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33845282438
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and see also page 7925
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Obtained via CBS reductions of their respective corresponding ketones: Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551 and see also page 7925.
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82
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note
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2 groups.
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83
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85030734815
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note
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2=c-hex.
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