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. 2020 May 5;10(30):17486–17491. doi: 10.1039/d0ra03006f

Solvent screening for HDA reaction.

graphic file with name d0ra03006f-u2.jpg
Entry Solvent Time (h) Yielda (%) drb Eec (%)
1 Toluene 48 86 80 20 92
2 Benzene 48 60 78 22 90
3 Xylene 48 73 77 23 88
4 Cyclohexane 48 66 74 26 89
5 Hexane 48 trace
6 Et2O 48 55 78 22 90
7 iPr2O 48 68 77 23 89
8 THF 48 40 79 21 82
9 CH2Cl2 48 74 79 21 90
10 CHCl3 48 34 84 16 92
11 C2H4Cl2 48 75 77 23 88
12 CH3CN 48 70 75 25 88
13 MeOH 48 38 68 32 83
14 Toluene 24 73 79 21 90
15 Toluene 72 86 78 22 86
16 Toluene 96 78 78 22 86
17 Neat 24 87 71 29 86
18 Neat 48 75 68 32 82
a

Isolated yield.

b

Diastereoselectivity (dr) was determined by 1HNMR of the crude reaction mixture (major diastereomer: 8a).

c

The ee value were determined by HPLC (Daicel chiralpak IB column).