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. 2015 Feb 11;51(12):2266–2269. doi: 10.1039/c4cc09495f

Table 1. Optimization of the asymmetric Michael addition a .

Inline graphic
Entry Solvent Cat. load (mol%) T (°C) t (h) Yield b (%) ee c (%)
1 CH2Cl2 5 rt 12 92 75
2 Toluene 5 rt 12 90 73
3 CHCl3 5 rt 12 86 61
4 Et2O 5 rt 12 88 63
5 CH2Cl2 5 0 0.5 93 89
6 Toluene 5 0 6 79 83
7 CH2Cl2 5 –20 2 93 92
8 CH2Cl2 5 –40 6 92 92
9 CH2Cl2 5 –78 6 92 92
10 CH2Cl2 7 –20 2 93 91
11 CH2Cl2 3 –20 2 93 92
12 CH2Cl2 1 –20 6 92 92

aReaction conditions: 0.28 mmol (1.1 equiv.) of 1a, 0.25 mmol (1.0 equiv.) of 2a, 1–7 mol% of catalyst D, 0.5 mL solvent.

bYield of isolated 3a after flash chromatography.

cThe enantiomeric excess was determined via the O-acetylated derivative 3a′ by HPLC analysis on a chiral stationary phase.