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letter
. 2014 Jan 6;10:12–17. doi: 10.3762/bjoc.10.3

Table 1.

Scope of the imine and isocyanide starting materials.

graphic file with name Beilstein_J_Org_Chem-10-12-i001.jpg
entry R1 R2 R3 yield
1 4-MeOC6H4 4-ClC6H4 t-Bu 3a (48%)
2 4-MeOC6H4 4-ClC6H4 c-C6H11 3b (41%)a
3 4-MeOC6H4 4-ClC6H4 Bn 3c (63%)a
4 4-MeC6H4 4-ClC6H4 4-MeOC6H4 3d (19%)b
5 3-MeOC6H4 4-ClC6H4 t-Bu 3e (19%) + 6 (27%)
6 4-MeOC6H4 2-ClC6H4 t-Bu 3f (12%) + 3f' (15%)
7 2-MeC6H4 4-ClC6H4 t-Bu 3g (31%)
8 n-C3H7 4-ClC6H4 t-Bu 3h' (32%)
9 4-MeOC6H4 EtOCO t-Bu 3i (9%)a + 7 (34%)
10 4-MeOC6H4 EtOCO c-C6H11 3j (34%)a
11 4-MeOC6H4 graphic file with name Beilstein_J_Org_Chem-10-12-i002.jpg t-Bu 3k (14%)b + 8 (17%)
12 4-MeC6H4 graphic file with name Beilstein_J_Org_Chem-10-12-i003.jpg t-Bu 3l (28%)
13 4-MeOC6H4 4-ClC6H4 Ts-CH2 –
14 4-MeOC6H4 4-ClC6H4 MeO2C-CH2 –

aThe reaction was performed at rt. 20% of catalyst was used. bThe adduct could not be isolated in pure form.