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. 2016 Jun 15;6(7):4694–4698. doi: 10.1021/acscatal.6b01400

Table 1. Catalyst Discovery for an Enantioselective Heine Reactiona.

graphic file with name cs-2016-01400n_0007.jpg

entry metal ligand conversion (%)b ee (%)b
1 Cu(OTf)2 L1 12 28
2 La(OTf)3 L1 24 –33
3 Cu(OTf)2 L2 95 39
4 Cu(OTf)2 L3 93 82
5 Ni(OTf)2 L3 23 –35
6 Pd(OTf)2 L3 41 60
7 Pd(OTf)2 L4 29 85
8 Pd(OTf)2 L5 27 95
9 7 0
10 Pd(OTf)2 L6 33 92
11c Pd(OTf)2 L6 79 94
12c Pd(ClO4)2 L6 60 76
13 Pd(BF4)2 L6 0
14c,d Pd(OTf)2 L6 89 88
a

Reaction conditions: aziridine 5 (0.1 mmol) and 50 mg of 4 Å powdered molecular sieves were added to the preformed catalyst (0.01 mmol of metal and 0.012 mmol of ligand) in CH2Cl2 (0.2 M) at room temperature for 24 h.

b

Determined by HPLC peak area ratios of 5 and 6 at 250 nm using the CHIRALCEL OJ column.

c

Reaction solvent was toluene.

d

Reaction performed with 5 mol % catalyst.