Table 1. Scope of Michael Addition of 1,1,1-Trifluoromethylketones 1 to Nitroolefins 2^a.

entry	1	2	3	yield (%)b	drc	erd
1	1a	C6H5	3aa	98	>20:1	95:5
2	1a	2-BrC6H4	3ab	95	>20:1	96.5:3.5
3	1a	2-NO2C6H4	3ac	94	>20:1	97.5:2.5
4	1a	2-CF3C6H4	3ad	96	>20:1	96.5:3.5e
5	1a	2-OMeC6H4	3ae	98	>20:1	94:6
6	1a	3-ClC6H4	3af	98	19:1	93.5:6.5
7	1a	4-BrC6H4	3ag	99	>20:1	95.5:4.5
8	1a	4-NO2C6H4	3ah	99	7:1	95.5:4.5
9	1a	4-CNC6H4	3ai	96	>20:1	96:4
10	1a	4-MeC6H4	3aj	96	8:1	93:7
11	1a	4-OMeC6H4	3ak	91	6:1	86.5:13.5
12	1a	2-thienyl	3al	97	16:1	91.5:8.5
13f	1a	3-N-Ts-indoyl	3am	92	>20:1	87.5:12.5
14	1a	CH=CHC6H5	3an	62 (65)g	>20:1	87:13
15	1a	cyclohexyl	3ao	42 (43)g	>20:1	94:6
16	1b	4-BrC6H4	3bg	97	>20:1	96:4
17	1c	4-BrC6H4	3cg	96	>20:1	88:12
18	1d	4-BrC6H4	3dg	97	>20:1	87:13
19	1e	4-BrC6H4	3eg	95	>20:1	93:7
20h	1f	C6H5	3fa	73 (82)g	>20:1	97:3

^aReactions were performed with 1 (0.21 mmol) and 2 (0.20 mmol) and proceeded to full conversion as adjudged by TLC.

^bIsolated yield. The diastereomers were not separable, and this represents the combined yield.

^cThe diastereomeric ratio was determined by ¹⁹F NMR spectroscopic analysis of the crude product.

^dThe enantiomeric ratio was determined by HPLC or SFC analysis on a chiral stationary phase.

^eThe enantiomeric ratio was determined following reduction of 3ad with NaBH₄ (see the SI).

^fThe reaction was performed at 0 °C for 3 h.

^gNumber in parentheses is conversion of nitroolefin as determined by ¹H NMR spectroscopic analysis of the crude product.

^hThe reaction was performed employing QD-TU (10 mol %) at 0 °C for 12 h.