Skip to main content
. 2023 Apr 25;14(20):5477–5482. doi: 10.1039/d3sc01060k

Condition optimizationa.

graphic file with name d3sc01060k-u2.jpg
Entry Solvent Base/L [Pd] Yieldb (%) drb eec (%)
Major/minor
1 THF DBU/L1 Pd(dba)2 94 14.7 : 1 98/31
2d THF DBU/L1 Pd(dba)2 >95 12.7 : 1 97/59
3e THF DBU/L1 Pd(dba)2 >95 12.7 : 1 97/30
4 MeCN DBU/L1 Pd(dba)2 91 14.2 : 1 98/42
5 DMF DBU/L1 Pd(dba)2 90 14.0 : 1 97/11
6 Toluene DBU/L1 Pd(dba)2 >95 11.4 : 1 96/69
7 THF Et3N/L1 Pd(dba)2 92 5.1 : 1 90/83
8 THF TMG/L1 Pd(dba)2 >95 8.7 : 1 95/84
9 THF KOtBu/L1 Pd(dba)2 >95 11.0 : 1 97/55
10 THF DBU/L2 Pd(dba)2 >95 4.0 : 1 79/31
11 THF DBU/L3 Pd(dba)2 >95 9.8 : 1 98/77
12 THF DBU/L4 Pd(dba)2 >95 18.6 : 1 95/30
13 THF DBU/L5 Pd(dba)2 >95 15.0 : 1 98/65
14 THF DBU/L4 Pd2(dba)3 >95 15.3 : 1 98/54
15 THF DBU/L4 [Pd(C3H5)Cl]2 86 13.3 : 1 98/16
16 THF DBU/L4 Pd(OAc)2 >95 15.0 : 1 98/9
17f THF DBU/L4 Pd(dba)2 >95 31.0 : 1 98/11
18g THF DBU/L4 Pd(dba)2 92h 32.3 : 1 99/52
a

Reaction conditions: 1c (0.1 mmol), 2a (1.5 equiv.), [Pd] (10 mol%), L (11 mol%), base (1.2 equiv.), solvent (1.0 mL), 5 Å MS (50 mg), 30 °C, 10–72 h.

b

Yield and diastereomeric ratio were measured by analysis of 1H NMR spectra using 1,3,5-trimethoxybenzene as the internal standard.

c

Determined by chiral HPLC.

d

2a′ instead of 2a.

e

2a′′ instead of 2a.

f

0 °C instead of 30 °C.

g

−20 °C instead of 30 °C.

h

Isolated yield for the reaction at the 0.2 mmol scale, 72 h.