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. Author manuscript; available in PMC: 2015 Jul 7.
Published in final edited form as: Chemistry. 2014 Jun 6;20(28):8691–8701. doi: 10.1002/chem.201402433

Table 3.

Nickel-Catalyzed Conversion of Monosaccharide Acetimidates.[a]

graphic file with name nihms-608086-f0004.jpg
Entry Acetimidates Time (h) Products (h) Yield (%)/[b] (α:β)[c]
1 graphic file with name nihms-608086-t0005.jpg 1 graphic file with name nihms-608086-t0006.jpg 91 (10:1)
2 graphic file with name nihms-608086-t0007.jpg 10 graphic file with name nihms-608086-t0008.jpg 90 (20:1)
3 graphic file with name nihms-608086-t0009.jpg 0.5 graphic file with name nihms-608086-t0010.jpg 87 (15:1)
4 graphic file with name nihms-608086-t0011.jpg 0.5 graphic file with name nihms-608086-t0012.jpg 91 (α only)
5 graphic file with name nihms-608086-t0013.jpg 12 graphic file with name nihms-608086-t0014.jpg 72 (α only)
[a]

The rearrangements were performed at 0.2 M in CH2G2 with 2 mol% of Ni(dppe)(OTf)2.

[b]

Isolated Yield.

[c]

1H NMR ratio.