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. 2022 Nov 23;8(47):eade3431. doi: 10.1126/sciadv.ade3431

Table 1. Optimization of reaction conditions.

graphic file with name sciadv.ade3431-t1.jpg

Entry Cu catal. Organocatal. Additive Yield (%)* ee %
1 CuOTf C1 (84)
2 CuOTf C2 (76)§
3 CuOTf A1 47 63
4 CuOTf A1 P1 52 91||
5 CuOTf A2 P1 52 76||
6 CuOTf A3 P1 74 84||
7 CuOTf A4 P1 65 93||
8 CuOTf A5 P1 73 89||
9 CuOTf A6 P1 53 87||
10 CuOTf A4 P2 31 73||
11 CuOTf A4 P3 81 73||
12 CuOTf A4 P4 67 63||
13 CuOTf A4 P1 76 93
14 (CuOTf)2•toluene A4 P1 78 93
15 (CuOTf)2 A4 P1 70 92
16 (CuOTf)4PF6 A4 P1 77 93
17 CUBr A4 P1 (87)

*Determined by GC using n-dodecane as an internal standard.

†Determined by chiral high-performance liquid chromatography.

‡The imine intermediate obtained in 84% yield.

§The imine intermediate obtained in 76% yield.

||Twenty mole percent of additive was used.

¶The imine intermediate obtained in 87% yield.