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. Author manuscript; available in PMC: 2010 Jul 21.
Published in final edited form as: Bioorg Med Chem. 2007 Dec 4;16(5):2212–2225. doi: 10.1016/j.bmc.2007.11.078

Table 3.

Reduction of β-keto phosphonate

graphic file with name nihms213606u3.jpg
Entry Hydride Conditions Yield (%) Ratio (a:b)a
1 NaBH4 EtOH, 0 °C 75 1:2.5
2 NaBH4, CeCl3 EtOH, −78 °C 82 1:1
3 NaBH4, CeCl3 EtOH, 0 °C 85 1:1
4 NaBH4, MgCl2 EtOH, 0 °C 60 1:1
5 Li(C2H5)3BH THF, 0 °C 33 1:9
6 LiAl[OC(C2H5)3]3H THF, 0 °C 40 1:11
7 Catecholborane THF, 0 °C NRb NR
a

a refers to the diastereomer that elutes first, b refers to the diastereomer that elutes second.

b

NR, no reaction.