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. 2010 Jul 16;107(48):20672–20677. doi: 10.1073/pnas.1003350107

Table 3.

Michael–Henry reaction to dideoxy-D-mannopyranose derivatives 7*graphic file with name pnas.1003350107figX11.jpg

Entry Product Time (T1, h) Time (T2, h) Yield (%) ee (%)
1 graphic file with name pnas.1003350107figX12.jpg 4 1 51 98
2 graphic file with name pnas.1003350107figX13.jpg 4 1 65 96
3 graphic file with name pnas.1003350107figX14.jpg 23 1 48 95
4 graphic file with name pnas.1003350107figX15.jpg 5 1 57 98
5 graphic file with name pnas.1003350107figX16.jpg 7 1 59 96
6 § graphic file with name pnas.1003350107figX17.jpg 20 2 66 93
7 § graphic file with name pnas.1003350107figX18.jpg 5 1 50 96

*3 (20 mol%) and 2 (0.2 mmol) were reacted with 1 (4 equiv.) in CH2Cl2 at 30 °C for T1, then DBU (50 mol%) was added and reacted for T2.

Yield of isolated product.

Determined by chiral phase HPLC analysis.

§3 (50 mol%) was used.