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. Author manuscript; available in PMC: 2008 Sep 15.
Published in final edited form as: J Am Chem Soc. 2006 Jun 14;128(23):7442–7443. doi: 10.1021/ja062091r

Table 1.

Enantioselective Synthesis of α-Hydroxy Phosphonatesa

graphic file with name nihms-63681-t0003.jpg
entry R1 R2 T
(°C)		 time
(h)		 yield
(%)b 		ee
(%)c
1 Ph Et rt 24 85 71
2 Ph Et −30 96 65 87
3 Ph Me −30 96 66 95
4 Ph i-Pr −30 120 60 96
5 p-Cl-C6H4 Et −30 96 68 91
6 p-Cl-C6H4 i-Pr −30 96 63 95
7 p-F-C6H4 Et −30 120 47 80
8 p-F-C6H4 i-Pr −30 120 68d 96
9 p-Br-C6H4 Et −30 96 66 >99
10 p-I-C6H4 Et −30 96 67 94
11 p-Me-C6H4 Et −30 96 63d 85
12 p-MeO-C6H4 Et −30 96 32d 86
13 Me Et rt 24 94 92
14 Me Et 0 72 91 97
15 PhCH2 Et rt 24 86d 92
16 PhCH2CH2 Et rt 48 76 81
17 trans-CH3CH=CH Et −30 108 67 98
a

All reactions were carried out with the ketophosphonate (0.50 mmol) in dry acetone (2.0 mL), with L-proline (0.10 mmol, 20 mol %) as the catalyst for the specified reaction time and temperature, unless otherwise specified.

b

Yield of isolated product after column chromatography.

c

Enantioselectivity was determined by HPLC analyses, the absolute configuration of the major enantiomer not determined.

d

With L-proline (0.25 mmol, 50 mol %) as the catalyst.