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. Author manuscript; available in PMC: 2020 Jan 18.
Published in final edited form as: J Org Chem. 2019 Jan 8;84(2):994–1005. doi: 10.1021/acs.joc.8b02893

Table 2.

Substrate Scope of Trifluoromethyl Imines with Various Acrylatesa

graphic file with name nihms-1010788-t0003.jpg

entry R1; 1 4 t (h) yield of 5 (%)b ee of 5 (%)c
1d Me; 1A 4a 8 80 (85); 5Aa 92(92)
2e Me; 1A 4b 3 89 (92); 5Ab 91 (93)
3d Me; 1A 4c 20 70 (75); 5Ac 85 (90)
4d Me; 1A 4d 20 50 (63); 5Ad 81 (86)
5e Me; 1A 4e 8 91 (93); 5Ae 94 (94)
6d Et; 1B 4a 5 71 (73); 5Ba 87 (90)
7 n-Bu; 1C 4a 8 63 (68); 5Ca 91 (91)
8 CH2=CH(CH2)3; 1D 4a 8 64 (68); 5Da 90 (92)
9 Ph(CH2)2; 1E 4a 8 53 (55); 5Ea 90 (88)
10f H; 1F 4a 4 62 (70); 5Fa 90 (91)
11 Cy; 1G 4a 8 -- (--); 5Ga -- (--)
12 Cy; 1G 4b 8 65 (63); 5Gb 91 (93)
13 CyCH2; 1H 4b 8 71 (72); 5Hb 90 (93)
14 Bn; 1I 4b 8 63 (72); 5Ib 90 (92)
15 4-BrBn; 1J 4b 8 68 (66); 5Jb 88 (91)
a

Unless noted, reactions were performed with 1 (0.2 mmol), acrylates 4 (0.4 mmol), A-1 (2.0 mol %), ethanol (20 μL) and aqueous KOH solution (2.2 μL, 50 wt %, 10 mol %) in PhMe (2.0 mL) with catalyst QD-3 (5.0 mol %) at the indicated temperature; results in parentheses were obtained from reactions catalyzed by epiQ-3 (5.0 mol %) in same conditions.

b

Isolated yield of 5.

c

Determined by HPLC analysis.

d

Reaction was performed at −40 °C.

e

1.0 mol % catalyst was used.

f

Reaction was performed at −50 °C