Skip to main content
. 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 4.

Substrate Scope of Trifluoromethyl Imines with α,β-Unsaturated Lactonesa

graphic file with name nihms-1010788-t0005.jpg

entry R1; 1 8 t (h) Yield of 9 (%)b ee of 9 (%)c
1d Me; 1A 8a 1 93 (94); 9Aa 99 (98)
2d n-Bu; 1C 8a 3 89 (90); 9Ca 99 (98)
3e Cy; 1G 8a 5 84 (82); 9Ga 99 (98)
4 PhCH=CH; 1K 8a 2 75 (71); 9Ka 99 (98)
5 Ph; 1L 8a 2 70 (69); 9La >99 (>99)
6 3-OMeC6H4; 1M 8a 2 55 (51); 9Ma >99 (>99)
7 4-ClC6H4; 1N 8a 2 50 (48); 9Na >99 (>99)
8e Me; 1A 8b 3 86 (91); 9Ab 94 (91)
a

Unless noted, reactions were performed with 1 (0.2 mmol), 8 (0.4 mmol), aqueous KOH solution (2.2 μL, 50wt %, 10 mol %), A-2 (10 mol % for entries 1–3 and 8, 50 mol % for entries 4­7) in PhMe (2.0 mL) with catalyst QD-1 (0.5 mmol %); results in parentheses were obtained from reactions catalyzed by epiQ-1 (0.5 mol %) in same conditions..

b

Isolated yield of 9, dr of 9 >95/5.

c

Determined by HPLC analysis.

d

1.0 mol % catalysts were employed.

e

2.0 mol % catalysts were employed.