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. Author manuscript; available in PMC: 2014 Apr 19.
Published in final edited form as: J Org Chem. 2013 Apr 10;78(8):4107–4114. doi: 10.1021/jo400428m

Table 3.

Reactions of Michael acceptors with tetrahydroisoquinoline 5.a

entry enone product time yieldb (d.r.)c
graphic file with name nihms463032t11.jpg graphic file with name nihms463032t12.jpg
1 R = Et 4 h 99%
2 R = Ph 2 h 91%
3 R = OMe 1 h 12%d
4 R = H 1 h 96%
5 graphic file with name nihms463032t13.jpg graphic file with name nihms463032t14.jpg 5 h 93% (2:1 d.r.)
6 graphic file with name nihms463032t15.jpg graphic file with name nihms463032t16.jpg 72 h 46%d (2:1 d.r.)
a

Unless otherwise noted, reactions were conducted using 2 mol% Ru(bpy)3Cl2, 2 equiv of MVK, and 1 equiv of TFA in degassed MeCN (0.25 M) at 50 °C and were irradiated using a 23 W compact fluorescent light bulb at a distance of 30 cm.

b

Values represent the averaged isolated yields of two reproducible experiments unless otherwise noted.

c

Diastereomer ratios determined by 1H NMR.

d

Yield determined by 1H NMR using an internal standard.