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. Author manuscript; available in PMC: 2014 Feb 20.
Published in final edited form as: Angew Chem Int Ed Engl. 2010;49(1):153–156. doi: 10.1002/anie.200904779

Table 2.

Michael addition of diphenyl phosphite (2) to trans-β-nitrostyrene (1a) catalyzed by 5[a].

graphic file with name nihms279124u2.jpg
entry solvent temp [°C] time conv [%][b] ee [%]
1 toluene rt 1 h 90 94
2 Et2O rt 1 h 81 93
3 tBuOMe rt 1 h 71 94
4 THF rt 1 h 99 93
5 MeCN rt 1 h 89 90
6 acetone rt 1 h 64 93
7 CH2Cl2 rt 15 min 99 96
8 CH2Cl2 0 30 min 99 (95[c]) 97
9 CH2Cl2 −10 1 h 99 98
10 CH2Cl2 −20 2 h 99 98.4
[a]

Reactions were carried out on 0.20 mmol of 1a with 1.25 equiv of 2 and 10 mol% 5 in 1.0 mL solvent.

[b]

Reaction conversions were determined by 1H-NMR.

[c]

Isolated yield.