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. 2022 Mar 16;87(7):4538–4549. doi: 10.1021/acs.joc.1c02817

Table 2. Optimization of the Reaction Conditionsa.

graphic file with name jo1c02817_0009.jpg

entry catalyst solvent additive t (days) yield of 3aa (%)b ee of 3aac
1 V CH2Cl2   3 37 77
2 V CHCl3   4 33 77
3 V Cl CH2CH2Cl   3 42 61
4 V CCl4   3 49 49
5 V Et2O   2 43 64
6 V toluene   2 58 54
7 V CH2Cl2 MS (5 Å)d 4 43 69
8 V CH2Cl2 CF3CH2OHe 4 47 69
9 V CH2Cl2 K2CO3e 3 39 0
10 V CH2Cl2 PhCO2Hf 5    
11g V CH2Cl2   3 44 71
12h V CH2Cl2   3 46 67
13 V CH2Cl2   5 46 74
14 VI CH2Cl2   4 52 76
15 VI CH2Cl2   5 61 74
16 IX CH2Cl2   3 51 74
17 IX CH2Cl2   5 46 77
a

Reaction conditions: 0.1 mmol of 1a, 0.1 mmol of 2a, 5 mol % of catalyst in 1 mL of solvent at rt.

b

Isolated yield of 3aa.

c

Determined by chiral HPLC.

d

50 mg of MS 5 Å.

e

0.1 mmol of additive was used.

f

0.025 mmol of PhCO2H was used.

g

0.12 mmol of 1a.

h

0.12 mmol of 2a.