Table 2.

Optimization of reactant, ligand, and reaction conditions for the enantioselective Mukaiyama-Michael addition.^[a]

entry	1	ligand	solvent	additive	yield (%)[b]	ee (%)[c]
1	1a	L1	DCM	-	43	54
2	1b	L1	DCM	-	64	12
3	1c	L1	DCM	-	33	50
4	1d	L1	DCM	-	42	93
5	1d	L2	DCM	-	30	65
6	1d	L3	DCM	-	33	76
7	1d	L4	DCM	-	40	87
8	1d	L5	DCM	-	34	88
9	1d	L6	DCM	-	<5	ND
10	1d	L1	DCM	HFIP (1.0 eq)	67	83
11	1d	L1	DCM	4Å (0.1g)	44	94
12	1d	L1	THF	4Å (0.1g)	<5	ND
13	1d	L1	Toluene	4Å (0.1g)	35	90
14[d]	1d	L1	DCM	HFIP (1.0 eq)	78	93
15[e]	1d	L1	DCM	HFIP & 4Å	81	94

^[a]Reactions were performed as described in Table 1. The chiral catalyst was prepared according to ref 12.

^[b]Isolated yield of 8 after chromatography.

^[c]Determined by chiral HPLC (See supporting information).

^[d]30 mol% Catalyst was used.

^[e]Catalyst was prepared in a glove box, and the reaction was run for three days.