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. Author manuscript; available in PMC: 2016 Feb 25.
Published in final edited form as: J Am Chem Soc. 2015 Feb 16;137(7):2452–2455. doi: 10.1021/ja512746q

Table 3.

Reactions of Structurally Varied Michael Acceptors with α-Silylamine 1.a

entry amine product time yield (%)b ee (%)c
graphic file with name nihms716466t15.jpg graphic file with name nihms716466t16.jpg
1 R = n-Pr 6 h 76 93
2 R = i-Pr 6 h 71 93
3 R = CH2OBn 6 h 75 91
4 R = t-Bu 12 h 35 96
graphic file with name nihms716466t17.jpg graphic file with name nihms716466t18.jpg
5 R = H 12 h 74 93
6 R = p-Cl 12 h 63 91
7 R = p-OMe 12 h 83 94
8 R = o-Me 12 h 81 85
9 graphic file with name nihms716466t19.jpg graphic file with name nihms716466t20.jpg 12 h 83 91
a

Unless otherwise noted, reactions were conducted using 1.5 equiv of Michael acceptor, 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.

b

Values represent the averaged isolated yields of two reproducible experiments.

c

Enantiomeric excess determined by chiral SFC analysis.