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. 2020 Mar 11;11(15):3852–3861. doi: 10.1039/d0sc00475h

Influence of the catalyst structure.

graphic file with name d0sc00475h-u1.jpg
Entry Cat. X (mol%) Solvent Time (d) Yielda (%) syn : antib eec (%)
1d DABCO 20 DCM 2 45 1 : 1.2
2 3a 20 Toluene 4 80 5.4 : 1 88
3e 3a 20 Toluene 7 76 7.0 : 1 93
4 4a 20 Toluene 4 80 1 : 11 56
5f 4a 5 DCE 2 95 1 : 24 70
6f 4b 5 DCE 2 90 1 : 15 95
7 8 20 Toluene 4 52 3.9 : 1 72
8 9 20 Toluene 4 51 3.5 : 1 73
9 6a 20 Toluene 4 33 1.6 : 1 56
10 10 20 Toluene 4 79 1 : 5.2 63
11 11 20 Toluene 1 89 1 : 3.0 61
12 12 20 Toluene 1 63 1.2 : 1 84
a

Isolated yield.

b

Determined by 1H NMR analysis of the crude mixture.

c

Determined by HPLC analysis.

d

Room temperature.

e

0.3 mmol, with 90 mg powdered 5 Å MS, [1a] = 0.3 M.

f

[1a] = 0.1 M. [1a] = 0.2 M without noted. DCM: CH2Cl2. DCE : CH2ClCH2Cl.