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1 Supporting Information Enantioselective Hydrogenation of β-ketophosphonates with Chiral Ru(II) Catalysts Xiaoming Tao, Wanfang Li, Xin Ma, Xiaoming Li, Weizheng Fan, Lvfeng Zhu, Xiaomin Xie, and Zhaoguo Zhang * School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai , China, State Key Laboratory of rganometallic Chemistry, Shanghai Institute of rganic Chemistry, 345 Lingling Road, Shanghai , China zhaoguo@sjtu.edu.cn Table of contents NMR data for compounds HLC for racemic and chiral compounds 2, 3m-s
2 NMR data for compounds 1-3 (1a) Dimethyl (2-oxo-2-phenyl)phosphonate Me Me Me Me 2
3 (2b) Diethyl (2-oxo-2-phenylethyl)phosphonate Et Et Et Et 3
4 (1c) Diisopropyl (2-oxo-2-phenylethyl)phosphonate 4
5 (1d) Dimethyl 2-o-methoxyphenyl-2-oxoethylphosphonate Me Me Me Me Me Me 5
6 (1e) Dimethyl 2-o-methylphenyl-2-oxoethylphosphonate CH 3 Me Me CH 3 Me Me 6
7 (1f) Dimethyl 2-m-methylphenyl-2-oxoethylphosphonate H 3 C Me Me H 3 C Me Me 7
8 (1g) Dimethyl 2-p-methylphenyl-2-oxoethylphosphonate Me Me H 3 C Me Me H 3 C 8
9 (1h) Dimethyl 2-p-methoxyphenyl-2-oxoethylphosphonate Me Me Me Me Me Me 9
10 (1i) Dimethyl 2-p-fluorophenyl-2-oxoethylphosphonate Me Me F Me Me F 10
11 (1j) Dimethyl 2-p-chlorophenyl-2-oxoethylphosphonate Me Me Cl Me Me Cl 11
12 (1k) Dimethyl 2-p-bromophenyl-2-oxoethylphosphonate Me Me Br Me Me Br 12
13 (1l) Dimethyl 2-p-trifuoromethylphenyl-2-oxoethylphosphonate Me Me F 3 C Me Me F 3 C 13
14 (1m) Dimethyl 2-oxopropylphosphonate Me Me Me Me 14
15 (1n) Dimethyl 2-oxobutylphosphonate Me Me Me Me 15
16 (1o) Dimethyl 3-methyl-2-oxobutylphosphonate Me Me Me Me 16
17 (1p) Dimethyl 2-oxoheptylphosphonate n-c 5 H 11 Me Me n-c 5 H 11 Me Me 17
18 (1q) Dimethyl 2-oxotridecylphosphonate C 11 H 23 Me Me C 11 H 23 Me Me 18
19 (1r) Dimethyl 2-cyclohexyl-2-oxoethylphosphonate Me Me Me Me 19
20 (1s ) Dimethyl 2-oxo-3-(N-tert-butoxycarbonylamino)propane phosphonate BocHN Me Me BocHN Me Me 20
21 (1t) Dimethyl (1-methylacetonyl)phosphonate Me Me Me Me 21
22 (1u) Dimethyl (1-ethylacetonyl)phosphonate Me Me Me Me 22
23 (1v) Diethyl (1-methylacetonyl)phosphonate Et Et Et Et 23
24 (1w) Dimethyl 1-bromo-2-oxopropylphosphonate Me Me Br Me Me Br 24
25 (2a) Dimethyl 2-hydroxy-2-phenylethylphosphonate H Me Me H Me Me 25
26 (2b) Diethyl 2-hydroxy-2-phenylethylphosphonate H Et Et H Et Et 26
27 (2c) Diisopropyl 2-hydroxy-2-phenylethylphosphonate H H 27
28 (2d) Dimethyl [2-hydroxy-2-(2-methoxyphenyl)ethyl]phosphonate Me H Me Me Me H Me Me 28
29 (2e) Dimethyl [2-hydroxy-2-(2-methylphenyl)ethyl]phosphonate CH 3 H Me Me CH 3 H Me Me 29
30 (2f) Dimethyl [2-hydroxy-2-(3-methylphenyl)ethyl]phosphonate H 3 C H Me Me H 3 C H Me Me 30
31 (2g) Dimethyl [2-hydroxy-2-(4-methylphenyl)ethyl]phosphonate H Me Me H 3 C H Me Me H 3 C 31
32 (2h) Dimethyl [2-hydroxy-2-(4-methoxyphenyl)ethyl]phosphonate H Me Me Me H Me Me Me 32
33 (2i) Dimethyl [2-hydroxy-2-(4-fluorophenyl)ethyl]phosphonate H Me Me F H Me Me F 33
34 (2j) Dimethyl [2-hydroxy-2-(4-chlorophenyl)ethyl]phosphonate H Me Me Cl H Me Me Cl 34
35 (2k) Dimethyl [2-hydroxy-2-(4-bromophenyl)ethyl]phosphonate H Me Me Br H Me Me Br 35
36 (2l) Dimethyl [2-hydroxy-2-(4- trifuoromethylphenyl)ethyl]phosphonate H Me Me F 3 C H Me Me F 3 C 36
37 (2m) Dimethyl 2-hydroxypropylphosphonate H Me Me H Me Me 37
38 (2n) Dimethyl 2-hydroxybutylphosphonate H Me Me H Me Me 38
39 (2o) Dimethyl (2-hydroxy-3-methylbutyl)phosphonate H Me Me H Me Me 39
40 (2p) Dimethyl 2-hydroxyheptylphosphonate C 5 H 11 H Me Me C 5 H 11 H Me Me 40
41 (2q) Dimethyl 2-hydroxytridecylphosphonate C 11 H 23 H Me Me C 11 H 23 H Me Me 41
42 (2r) Dimethyl 2-hydroxycyclohexylphosphonate H Me Me H Me Me 42
43 (2s) Dimethyl 2-hydroxy-3-(N-tert-butoxycarbonylamino)phosphonate BocHN H Me Me BocHN H Me Me (2t) Dimethyl 3-hydroxybut-2-ylphosphonate 43
44 H Me Me H Me Me 44
45 (2u) Dimethyl (2-hydroxypentan-3-yl)phosphonate H Me Me H Me Me 45
46 (2v) Diethyl 3-hydroxybut-2-ylphosphonate H Et Et H Et Et 46
47 (2w) Dimethyl 1-bromo-2-hydroxypropylphosphonate H Me Me Br H Me Me Br 47
48 (3m) 1-(Dimethoxyphosphoryl)propan-2-yl 4-nitrobenzoate N 2 Me Me N 2 Me Me 48
49 (3n) 1-(Dimethoxyphosphoryl)butan-2-yl 4-nitrobenzoate N 2 Me Me N 2 Me Me 49
50 (3o) 1-(Dimethoxyphosphoryl)-3methylbutan-2-yl 4-nitrobenzoate N 2 Me Me N 2 Me Me 50
51 (3p) 1-(Dimethoxyphosphoryl)heptan-2-yl 4-nitrobenzoate N 2 C 5 H 11 Me Me N 2 C 5 H 11 Me Me 51
52 (3q) 1-(Dimethoxyphosphoryl)tridecan-2-yl 4-nitrobenzoate N 2 C 11 H 23 Me Me N 2 C 11 H 23 Me Me 52
53 (3r) 1-Cyclohexyl-2-(dimethoxyphosphoryl)ethyl 4-nitrobenzoate N 2 Me Me N 2 Me Me 53
54 (3s) 1-[(Tert-butoxycarbonyl)amino-3-(dimethoxyphosphoryl)propan-2-yl 4- nitrobenzoate N 2 BocHN Me Me N 2 BocHN Me Me 54
55 (3t) 3-(Dimethoxyphosphoryl)butan-2-yl 4-nitrobenzoate N 2 Me Me N 2 Me Me 55
56 (3u) 3-(Dimethoxyphosphoryl)pentan-2-yl 4-nitrobenzoate N 2 Me Me N 2 Me Me 56
57 (3v) 3-(Diethoxyphosphoryl)butan-2-nitrobenzoate 2 N Et Et 2 N Et Et 57
58 (3w) 1-Bromo-1-(dimethoxyphosphoryl)propan-2-yl 4-nitrobenzoate 2 N Br Me Me 2 N Br Me Me 58
59 HLC for racemic and chiral compounds 2, 3m-s 2a Racemate: Table 1, entry 1: L1 as ligand 59
60 Table 1, entry 2: L2 as ligand Table 1, entry 3: L3 as ligand Table 1, entry 4: L4 as ligand 60
61 Table 1, entry 5: L5 as ligand Table 1, entry 6: L6 as ligand Table 1, entry 7: L7 as ligand 61
62 Table 1, entry 8: L8 as ligand Table 1, entry 9: L9 as ligand Table 1, entry 10: L10 as ligand Table 2, entry 1 62
63 Table 2, entry 2 Table 2, entry 3 63
64 Table 2, entry 4 Table 2, entry 5 Table 2, entry 6 64
65 Table 2, entry 7 Table 2, entry 8 Table 3, entry 1 65
66 Table 3, entry 2 Racemate: 66
67 Table 3, entry 3 Racemate: Table 3, entry 4 67
68 Racemate: Table 3, entry 5 Racemate: 68
69 Table 3, entry 6 Racemate: 69
70 Table 3, entry 7 Racemate: 70
71 Table 3, entry 8 H Me Me Me Racemate: 71
72 Table 3, entry 9 Racemate: 72
73 Table 3, entry 10 Racemate: Table 3, entry 11 73
74 Racemate: Table 3, entry 12 74
75 H Me Me F 3 C Racemate: Table 3, entry 13 75
76 Racemate: Table 3, entry 14 Racemate: 76
77 Table 3, entry 15 Racemate: 77
78 Table 3, entry 16 N 2 C 5 H 11 Me Me Racemate: 78
79 Table 3, entry 17 Racemate: 79
80 Table 3, entry 18 Racemate: Table 3, entry 19 80
81 N 2 BocHN Racemate: Me Me Table 3, entry 20 81
82 N 2 Me Me Racemate: Table 3, entry 21 82
83 Racemate: Table 3, entry 22 83
84 Racemate: Table 3, entry 23 84
85 Racemate: Table 3, entry 24 85
86 Table 4. ptimization of Temperature and Time entry T ( ) t (h) con (%) yield (2m:2u) ee (%) dr : : : : : : : : : :5 All reactions were carried out with 1u (1 mmol) concentration of 0.5 M in MeH under 10 atm of H 2, S/C = 200/1. Ee and dr values were determined by HLC. Table 5. ptimization of Time a entry time (h) con (%) b ee (%) c > > a All reactions were carried out with a substrate (1 mmol) concentration of 0.5 M in MeH under 10 bar of H 2 at 50 C, S/C= 200:1. b Conversion were determined by NMR. c Ee values were determined by HLC on a Chiralpak B-H column. Table 5, entry 1 86
87 Table 5, entry 2 Table 5, entry 3 87
88 Table 5, entry 4 88
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