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. 2011 Apr 7;7:410–420. doi: 10.3762/bjoc.7.53

Table 4.

A regioselective 1,3-hydrogen shift.a

entry allenamides conditions (time) amido-alkenes yield [%]b,c

1 graphic file with name Beilstein_J_Org_Chem-07-410-i030.jpg 29a: R = Ph 115 °C (16 h) graphic file with name Beilstein_J_Org_Chem-07-410-i031.jpg 33a 71
2 29b: R = H d 33b 90

3 graphic file with name Beilstein_J_Org_Chem-07-410-i032.jpg 30 115 °C (16 h) graphic file with name Beilstein_J_Org_Chem-07-410-i033.jpg 34 79

4 graphic file with name Beilstein_J_Org_Chem-07-410-i034.jpg 31a: R = H CSA (10 min) graphic file with name Beilstein_J_Org_Chem-07-410-i035.jpg 35a 68
5 31b: R = Me CSA (10 min) 35b 80

6 graphic file with name Beilstein_J_Org_Chem-07-410-i036.jpg 32 CSA (10 min) graphic file with name Beilstein_J_Org_Chem-07-410-i037.jpg 36 84

aUnless otherwise noted, CH3CN was the solvent for thermal conditions and CH2Cl2 was the solvent when using 10 mol % of CSA at rt. For all reactions, concn = 0.10 M. bAll were isolated yields. cAll amido-di- and trienes were exclusively E-selective [≥95:5]. dSee text for this isomerization.