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30th June 2010 @ 10:24
No product / mixture of compounds in the previous trial: Preparation of (+/-)-BINOL-N-triflyl phosphoramide (MW39) – repetition of the experiment under similar conditions:
Preparation of a strong achiral Brønsted acid, intended for pretests for the acid-catalysed Pictet-Spengler reaction

Reaction Scheme


Start time: 5:21 PM 29/06/2010
End time: 12:15 PM 30/06/2010

Procedure: [1]
To a mixture of (+/-)-BINOL (172 mg, 600 µmol) and Et3N (585 µL, 425 mg, 4.20 mmol, 7 eq.) in DCM (3 mL) was added POCl3 (110 mg, 67 µL, 720 µmol, 1.2 eq.) and DMAP (147 mg, 1.20 µmol, 2 eq.) at 0°. The mixture was warmed to room temperature and stirred for 1 h.
- evaporated DCM, added propionitrile (3 mL) and TfNH2 MW38 (179 mg, 1.20 mmol, 2 eq.) and heated reaction mixture to 100°C for 18 h

[1] “Design of Chiral N-Triflyl Phosphoramide as a Strong Chiral Brønsted Acid and Its Application to Asymmetric Diels-Alder Reaction", D. Nakashima and H. Yamamoto, J. Am. Chem. Soc. 2006, 128, 30, 9626–9627.
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