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. Author manuscript; available in PMC: 2010 Sep 17.
Published in final edited form as: Org Lett. 2009 Sep 17;11(18):4168–4171. doi: 10.1021/ol901703t

Table 2.

Dienamide formation from enyne 1 and isocyanates 2a-2j

entry E/Z products E:Z ratioa rxn temp % yieldb
1 graphic file with name nihms150616t1.jpg 5:1 rt, 1 h 70
2 graphic file with name nihms150616t2.jpg 2:1 rt, 2 h 68
3 graphic file with name nihms150616t3.jpg 2:1 80 °C, 1 h 75
4 graphic file with name nihms150616t4.jpg 2:1 60 °C, 2 h 79
5 graphic file with name nihms150616t5.jpg 2:1 60 °C, 2 h 74
6 graphic file with name nihms150616t6.jpg 1.8:1 100 °C, 2 h 57
7 graphic file with name nihms150616t7.jpg 2:1 80 °C, 5 h 66
8 graphic file with name nihms150616t8.jpg 2:1 80 °C, 1 h 71
9 graphic file with name nihms150616t9.jpg 2:1 80 °C, 1.5 h 80

Reaction conditions: 1 equiv 1a, 1 equiv 2,

a

Determined by 1H-NMR,

b

isolated yields, average of 2 runs