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. Author manuscript; available in PMC: 2014 Nov 20.
Published in final edited form as: Chemistry. 2014 Mar 3;20(14):3917–3921. doi: 10.1002/chem.201400407

Table 1.

Optimization of the reaction conditions for the Friedel–Crafts Michael-type reaction.[a]

graphic file with name emss-61040-t0008.jpg
Entry Solvent [mL] t [h] Yield [%][b] ee [%][c]
1 CHCl3 (1.5) 16 56 91
2 CH2Cl2 (1.5) 15 59 87
3 toluene (1.5) 21 60 88
4 PhCl (1.5) 21 61 87
5 toluene (3.0) 21 70 91
6 CH2Cl2(3.0) 24 68 91
7[d] CHCl3 (3.0) 65 89 93
8[d] toluene (3.0) 65 95 93
[a]

General reaction conditions: 2a (0.5 mmol), pyrrole 1a (1.0 mmol), 10 (20 mol %), TFA (30 mol%), rt.

[b]

Yield of isolated 3.

[c]

Determined by HPLC analysis on a chiral stationary phase.

[d]

The reaction was performed at 0 °C.