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. 2010 Feb 11;15(2):917–958. doi: 10.3390/molecules15020917

Table 6.

Substrate scopes for L-proline-catalyzed α-aminoxylation of aldehydes with nitrosobenzene.

graphic file with name molecules-15-00917-i007.jpg
R conditions yield (%)a ee (%)a ref.
Me, Et, nPr, iPr, Ph, Bn 30 mol% 1, MeCN, -20 ºC, 24 h 62–>99 95–99 [62]
Me, nBu, iPr, allyl, Bn, Ph, TIPSO(CH2)3, N-methylindol-3-ylmethyl 5 mol% 1, CHCl3, 4 ºC, 4 h 60–88 97–99 [63]
Me, nPr, iPr, nBu, allyl, Bn, BnOCH2, BocNH(CH2)4 20 mol% 1, DMSO, RT, 10–20 min 54–86 94–99 [64]

a Yield and ee were determined after NaBH4 reduction to the corresponding diols.