Table 2.

Reactions of Structurally Varied α-Silylamines with Michael acceptor 2b.^a

entry	amine	product	time	yield (%)b	ee (%)c
1	R = H		6 h	87	93
2	R = F		6 h	94	94
3	R = Cl		6 h	96	93
4	R = Br		6 h	90	92
5	R = Me		12 h	79	91
6	R = OMe		12 h	<5	--
7			6 h	85	92
8			6 h	80	96d,e
9			12 h	80	90
10			12 h	<5	--
11			12 h	93	91d,e
12	R = Bn		6 h	60	94
13	R = i-Pr		12 h	33	95
14	R = Boc		12 h	<5	--

^aUnless otherwise noted, reactions were conducted using 1.5 equiv of 2, 2 mol% Ru(bpy)₃Cl₂, 15 mol% Sc(OTf)₃, 20 mol% (S,S)-4c and 30 mol% Bu₄N⁺Cl⁻ in degassed MeCN (0.05 M) and were irradiated using a 23 W compact fluorescent light bulb.

^bValues represent the averaged isolated yields of two reproducible experiments.

^cEnantiomeric excess determined by chiral SFC analysis.

^dEnantiomeric excess of the corresponding alcohol.

^eReaction conducted using (R,R)-4c to facilitate measurement of ee.