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No reaction was observed with N-benzyl, N-phenyl, N-(4-methoxyphenyl), N-Boc, N-CBz, N-Bz, N-benzhydryl derivatives.
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No reaction was observed with N-benzyl, N-phenyl, N-(4-methoxyphenyl), N-Boc, N-CBz, N-Bz, N-benzhydryl derivatives.
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General Procedure for Direct Mannich Reaction In a typical experiment acetophenone 3 (2 equiv, aldimine 2, catalyst 1c (10 mol, and AcOH (20 mol, were suspended in Bu2O in a screw-capped vial and the resulting mixture was allowed to stir at r.t. for 60 h. Purification of the crude product by column chromatography on silica gel afforded the corresponding product 4. 3-(4-Chlorophenylamino)-1,3- diphenylpropan-1-one (4a) The title compound was isolated by column chromatography (n-hexane-EtOAc, 10:1) as a colorless solid in 43% yield and 86% ee. The ee was determined by HPLC using Chiralcel OD-H column [n-hexane-i-PrOH (90:10, flow rate 0.6 mL/min; major enantiomer: tR, 25.3 min; minor enantiomer: tR, 28.2 min, mp 162°C; [α]D +31.0 (c 1.0, CH 2Cl2, IRKBR, 3373, 2924, 1666, 1507, 1489, 1286, 1003, 820, 703 cm-1. ESI-HRM
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2O in a screw-capped vial and the resulting mixture was allowed to stir at r.t. for 60 h. Purification of the crude product by column chromatography on silica gel afforded the corresponding product 4. 3-(4-Chlorophenylamino)-1,3- diphenylpropan-1-one (4a) The title compound was isolated by column chromatography (n-hexane-EtOAc, 10:1) as a colorless solid in 43% yield and 86% ee.
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For a review on the concept of combined acids, see
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For a review on the concept of combined acids, see: Yamamoto, H.; Futatsugi, K. Angew. Chem. Int. Ed. 2005, 44, 1924;
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