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. Author manuscript; available in PMC: 2013 Mar 14.
Published in final edited form as: J Am Chem Soc. 2012 Mar 2;134(10):4941–4954. doi: 10.1021/ja210981a

Table 4. Initial study of the reaction of cyano donor 10 with tosyl imine 12.

graphic file with name nihms361505u5.jpg
entry Pd ligand temp (°C) solvent conc yield (%) 13a (ee) 14a (ee) 15a (ee)
1 CpPd(η3-C3H5) L13 50 PhCH3 0.2M 88 0 0.7 1
2 CpPd(η3-C3H5) L13 4 PhCH3 0.2M 100 0.2 (49%) 0 1 (27%)
3 Pd(dba)2 L13 4 PhCH3 0.2M 100 0.2 0 1
4 CpPd(η3-C3H5) L14 4 PhCH3 0.2M 97 0 0.4 (66%) 1 (42%)
5 CpPd(η3-C3H5) L15 4 PhCH3 0.2M 100 0.7 (3.5:1, 79%, ND) 0.7 (77%) 1 (15%)
6 CpPd(η3-C3H5) L16 4 PhCH3 0.2M 43 12 (1.4:1, -30%, −56%) 0 1 (ND)
7 CpPd(η3-C3H5) L12 4 PhCH3 0.2M 80 0.2 (92%) 0.2 (90%) 1 (32%)
8 CpPd(η3-C3H5) L17 4 PhCH3 0.2M 64 9 (1.2:1, 63%, 25%) 0 1 (69%)
9 CpPd(η3-C3H5) L18 4 PhCH3 0.2M 79 5.2 (1.8:1, 52%, 32%) 0 1 (30%)
10 CpPd(η3-C3H5) L2 4 PhCH3 0.2M 78 6 (1:1, 73%, 45% 0 1 (33%)
11 CpPd(η3-C3H5) L19 4 PhCH3 0.2M 100 0.5 (45%) 0 1 (10%)
12 CpPd(η3-C3H5) L20 4 PhCH3 0.2M 100 0.3 (39%) 0 1 (31%)
13 CpPd(η3-C3H5) L21 4 PhCH3 0.2M 79 0 3 (27%) 1 (33%)
14 CpPd(η3-C3H5) L22 4 PhCH3 0.2M 0
15 CpPd(η3-C3H5) L12 50 PhCH3 0.2M 93 0 0.8 (90%) 1 (43%)
16 CpPd(η3-C3H5) L12 80 PhCH3 0.2M 100 0 1.1 (70%) 1 (46%)
17 Pd(dba)2 L12 50 PhCH3 0.2M 100 0 0.5 (82%) 1 (41%)
18 Pd(OAc)2 L12 4 PhCH3 0.2M 100 0.2 (96%) 0.1 (92%) 1 (33%)
19 CpPd(η3-C3H5) L12 40 CH2Cl2 0.2M 83 0 0.9 (53%) 1 (12%)
20 CpPd(η3-C3H5) L12 4 THF 0.2M 100 0.2 (95%) 0.3 (91%) 1 (35%)
21 CpPd(η3-C3H5) L12 4 Dioxane 0.2M 100 0.2 (92%) 0.1 (91%) 1 (21%)
22 CpPd(η3-C3H5) L12 4 Et2O 0.2M Complex 0 0.5 1
23 CpPd(η3-C3H5) L12 4 PhCH3 0.01M 35 1.25 (95%) 0 1 (37%)
24 CpPd(η3-C3H5) L12 4 THF 0.01M 46 2.5 (95%) 0 1 (48%)
25 CpPd(η3-C3H5) L12 4 THF 0.02M 100 1.8 (95%) 1.7 (92%) 1 (50%)
26a CpPd(η3-C3H5) L12 4 THF 0.02M 90 2 (90%) 0 1 (50%)
27b CpPd(η3-C3H5) L12 4 THF 0.02M 100 0.3 (86%) 3.3 (82%) 1 (50%)
28 CpPd(η3-C3H5) L12 23 THF 0.02M 100 0 4 (81%) 1 (52%)
29 CpPd(η3-C3H5) L12 50 THF 0.02M 100 0 10 (81%) 1
30 CpPd(η3-C3H5) L12 4 PhCl 0.02M 48 0.5 (92%) 0 1 (33%)
31 CpPd(η3-C3H5) L12 4 DME 0.02M 100 2 (90%) 0.6 (85%) 1 (39%)
32c CpPd(η3-C3H5) L12 4 PhCH3 0.02M 0
a

In(acac)3 (10 mol%) was added.

b

DMSO (1 vol%) was added.

c

n-Hex4NCl (10 mol%) was added.