Preparation of Optically Pure Tertiary Phosphine Oxides via Addition of P-Stereogenic Secondary Phosphine Oxide to Activated Alkenes
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1 Preparation of Optically Pure Tertiary Phosphine Oxides via Addition of P-Stereogenic Secondary Phosphine Oxide to Activated Alkenes Ji-Ping Wang, Shao-Zhen Nie, Zhong-Yang Zhou, Jing-Jing Ye, Jing-Hong Wen, Chang-Qiu Zhao* College of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng, Shandong , China Table of Contents General Chemistry: Reagent and solvents: 31P NMR Yield measurements: Part 1. Investigation of the reaction under alkali condition Part 2. Investigation of the reaction thermal condition Part 3. Crystallographic Information Part 4. Selected 1H, 31P and 13C NMR spectroscopy of 3 and 5 S2 S2 S2 S3 S6 S7 S9 1
2 General Chemistry: 1 H NMR spectra were recorded on a 400-MHz spectrometer. Chemical shift for 1 H NMR spectra (in parts per million) relative to internal tetramethylsilane (Me 4 Si, δ= 0.00 ppm) with Chloroform-d. 13 C NMR spectra were recorded at 101 mhz Chemical shifts for 13 C NMR spectra are reported (in parts per million) relative to Chloroform-d (δ= 77.0 ppm). 31 P NMR spectra were recorded at 162 MHz, and chemical shifts reported (in parts per million) relative to external 85% phosphoric acid (δ= 0.0 ppm). TLC plates were visualized by UV.. Reagent and solvents: All starting material were purchased from commercial sources and used as received. The solvents were distilled under N 2 and dried according to standard procedures. 31 P NMR Yield measurements: 31 P NMR spectra were referenced to phosphoric acid. The NMR yields of the article are determined by integration of all the resonances in the 31 P spectra. The yields obtained by the approach are generally accurate and reproducible 2
3 Part 1. Investigation of the reaction under alkali condition General procedure, in DMSO or DMF: To the solution of 1 (50 mg, mmol), 2a (33 mg, mmol) in some solvent (0.5 ml), the base was added and the mixture was stirred at the temperature for the time as indicated in Table S-1. The suspension (0.1 ml) was added to saturated aqueous ammonium chloride, extracted with dichloromethane, washed with water and dried over anhydrous magnesium sulfate. After removing solvent, the residue was analyzed with proton and 31 P-NMR spectra, and the results were summarized in Table S-1. The 31 P and proton NMR spectroscopy of 3a/3a were shown in Figure S-1 and S-2. Table S-1. Base-catalyzed addition of 1 to benzaacetone 2a. entry solvent 1 DMSO 2 DMSO 3 DMSO 4 DMF Catalyst (mol %) KOH (25) KOH (25) LiOH (25) Ca(OH) 2 (25) temp. /time Peak of 3a on 31 P-NMR (45.07 ppm) % [a] Peak of 3a (46.68 ppm) % [a] 34 o C/25h o C/21h o C/70h o C/21 h Peak of unconsumed 1 on 31 P-NMR (33.26 ppm) % [a] 5 DMF 6 iproh 7 iproh 8 iproh 9 THF 10 THF 11 THF Ca(OH) 2 (25) KOH (25) KOH (25) KOH (25) nbuli (20) nbuli (50) nbuli (100) -5 o C/21 h o C/19h o C/0.5h o C/5h o C/11h o C/48h o C/3h [b] -78 o C/3h [b] -78 o C/3h [b] [a] The photocopy of NMR spectroscopy of 3a and 3a were presented in Figure S-1 and S-2. [b] By-products other than 3a/3a were detected. 3
4 General procedure, in isopropanol: The KOH (0.047 mmol) was dissolved previously in isopropanol (0.5 ml) with stirring. If necessary, the mixture can be heated to accelerate the dissolving, and the resulting solution was cooled to room temperature before using. To the clear solution of KOH, 1 (0.05 g,0.189 mmol) and 2a (0.033 g, mmol) were added. The mixture was stirred at the temperature for the time as indicated in Table S-1. The suspension (0.1 ml) was added to saturated aqueous ammonium chloride, extracted with dichloromethane, washed with water and dried over anhydrous magnesium sulfate. After removing solvent, the residue was analyzed with proton and 31 P-NMR spectra, and the results were summarized in Table S-1. Figure S P NMR spectroscopy of 3a and 3a. General procedure, for nbuli in THF: To the solution of 1 (0.053 g, 0.2 mmol) in THF (1 ml), the solution of nbuli (2.2 M solution in hexane, 0,091 ml, 0.2 mmol) was added at -78 o C. The resulting solution was stirred for 10 min at the same temperature, then 2a (0.032 g, 0.22 mmol) was added in one portion. After the mixture was stirred for 3 h, the mixed solvent of acetic acid/thf (2:1, 0.2 ml) was added dropwise at the same temperature to stop the reaction. The mixture was added to saturated aqueous ammonium chloride, extracted with dichloromethane, washed with water and dried over anhydrous magnesium sulfate. After removing solvent, the residue was analyzed with proton and 31 P-NMR spectra, and the results were summarized in Table S-1. 4
5 Figure S-2. Proton NMR spectroscopy of 3a and 3a. entry solvent Table S-2. Optimization of the thermal addition of 1 to 2a. Catalyst additive (mol %) or temp. 3a ( a (46.68 /time [a] ppm) % [a] ppm) % [a] 1 no no 80 o C /22 h toluene no 80 o C /17 h toluene no 80 o C /24 h toluene no 60 o C /24 h DMSO no 80 o C /46 h nc 8 H 18 no 80 o C /46 h [b] 7 pyridine no 80 o C /24 h MeOH no 60 o C /19 h [b] 9 toluene AIBN (20) 60 o C /25 h toluene AIBN (20) 80 o C /52 h toluene Ph3P (20) Rt/40h Nr 12 toluene Et3N (20) Rt/40h Nr 13 toluene TEMPO (20) 80 o C /24 h [b] 14 toluene TEMPO (20) 100 o C/41 h Complicated [c] Unconsumed 1 (33.26 ppm) % [a] [a] The photocopy of NMR spectroscopy of 3a and 3a were presented in Figure S-1 and S-2. [b] By-products other than 3a/3a were detected. [c] The epimerization of 1 and formation of the stereomers other than 3a/3a were detected. 5
6 Part 2. Investigation of the reaction under thermal condition General procedure, neat condition: The mixture of 1 (0.050 g, mmol) and 2a (0.033 g, mmol) was heated at 80 o C with stirring. The oily substance (ca ml) was dissolved in d-chloroform, analyzed with proton and 31 P-NMR spectra, and the results were summarized in Table S-2. General procedure, thermal addition in a solution: The solution of 1 (0.050 g, mmol), 2a (0.033 g, mmol) and additive (AIBN or TEMPO) in solvent (0.1 ml) was heated at 80 o C with stirring. The solution (ca ml) was dissolved in d-chloroform, analyzed with proton and 31 P-NMR spectra, and the results were summarized in Table S-2. 6
7 Part 3. Crystallographic Information (S P,S)-4-[( )-Menthylphenylphosphoryl]-1-(p-methoxyphenyl)-4-phenylpropan-2-one, 3e Empirical formula C32 H39 O3 P Crystal system Orthorhombic Space group P Formula weight a, Å (3) b, Å (10) c, Å (18) α, deg 90 β, deg 90 γ, deg 90 V, Å (3) Z 4 T, K 293(2) λ, Å ρ, g cm Rint R1 [I N 2σ(I)] R1 (all data) wr2 [I N 2σ(I)] wr2 (all data) Flack -0.01(3) CCDC
8 Fig S-1. ORTEP drawing of 3e with thermal ellipsoids at the 50% probability. 8
9 Part 4. Selected 1H, 31P and 13C NMR spectroscopy of 3 and 5 (S P,S)-4-[( )-Menthylphenylphosphoryl]-4-phenylbutan-2-one, 3a 31 P-NMR spectroscopy of crude 3a/3a =91:9 31 P-NMR spectroscopy of isolated 3a 9
10 1 H-NMR spectroscopy of isolated 3a 13 C-NMR spectroscopy of isolated 3a 10
11 (S P,S)-4-[( )-Menthylphenylphosphoryl]-1-phenyl-4-phenylpropan-2-one, 3b 31 P-NMR spectroscopy of crude 3b/3b =88:12 31 P-NMR spectroscopy of isolated 3b 11
12 1 H-NMR spectroscopy of isolated 3b 13 C-NMR spectroscopy of isolated 3b 12
13 (S P,S)-4-[( )-Menthylphenylphosphoryl]-1-(p-chlorophenyl)-4-phenylpropan-2-one, 3c 31 P-NMR spectroscopy of crude 3c/3c =89:11 31 P-NMR spectroscopy of isolated 3c 13
14 1 H-NMR spectroscopy of isolated 3c 13 C-NMR spectroscopy of isolated 3c 14
15 (S P,S)-4-[( )-Menthylphenylphosphoryl]-1-(p-bromophenyl)-4-phenylpropan-2-one, 3d 31 P-NMR spectroscopy of crude 3d/3d =89:11 31 P-NMR spectroscopy of isolated 3d 15
16 1 H-NMR spectroscopy of isolated 3d 13 C-NMR spectroscopy of isolated 3d 16
17 (S P,S)-4-[( )-Menthylphenylphosphoryl]-1-(p-methoxyphenyl)-4-phenylpropan-2-one, 3e 31 P-NMR spectroscopy of crude 3e/3e =87:13 31 P-NMR spectroscopy of isolated 3e 17
18 1 H-NMR spectroscopy of isolated 3e 13 C-NMR spectroscopy of isolated 3e 18
19 (S P,S)-4-[( )-Menthylphenylphosphoryl]-1-phenyl-4-(o-fluorophenyl)propan-2-one, 3f 31 P-NMR spectroscopy of crude 3f/3f =93:7 31 P-NMR spectroscopy of isolated 3f 19
20 1 H-NMR spectroscopy of isolated 3f 13 C-NMR spectroscopy of isolated 3f 20
21 (S P,S)-4-[( )-Menthylphenylphosphoryl]-1-phenyl-4-(o-chlorophenyl)propan-2-one, 3g 31 P-NMR spectroscopy of crude 3g/3g =95:5 31 P-NMR spectroscopy of isolated 3g 21
22 1 H-NMR spectroscopy of isolated 3g 13 C-NMR spectroscopy of isolated 3g 22
23 (S P,S)-4-[( )-Menthylphenylphosphoryl]-1-phenyl-4-(o-bromophenyl)propan-2-one, 3h 31 P-NMR spectroscopy of crude 3h/3h =94:6 31 P-NMR spectroscopy of isolated 3h 23
24 1 H-NMR spectroscopy of isolated 3h 13 C-NMR spectroscopy of isolated 3h 24
25 (S P,S)-4-[( )-Menthylphenylphosphoryl]-1-phenyl-4-(o-methoxyphenyl)propan-2-one, 3i 31 P-NMR spectroscopy of crude 3i/3i =89:11 31 P-NMR spectroscopy of isolated 3i 25
26 1 H-NMR spectroscopy of isolated 3i 13 C-NMR spectroscopy of isolated 3i 26
27 (S P,S)-4-[( )-Menthylphenylphosphoryl]-1-phenyl-4-(p-chlorophenyl)propan-2-one, 3j 31 P-NMR spectroscopy of crude 3j/3j =91:9 31 P-NMR spectroscopy of isolated 3j 27
28 1 H-NMR spectroscopy of isolated 3j 13 C-NMR spectroscopy of isolated 3j 28
29 (S P,S)-4-[( )-Menthylphenylphosphoryl]-1-phenyl-4-(p-methoxyphenyl)propan-2-one, 3k 31 P-NMR spectroscopy of crude 3k/3k =85:15 31 P-NMR spectroscopy of isolated 3k 29
30 1 H-NMR spectroscopy of isolated 3k 13 C-NMR spectroscopy of isolated 3k 30
31 (S P,S)-4-[( )-Menthylphenylphosphoryl]-1-(p-methoxyphenyl)-4-(o-trifluoromethylphenyl)pr opan-2-one, 3l 31 P-NMR spectroscopy of crude 3l/3l =95:5 31 P-NMR spectroscopy of isolated 3l/3l =98:2 1 31
32 H-NMR spectroscopy of isolated 3l/3l =98:2 13 C-NMR spectroscopy of isolated 3l/3l =98:2 32
33 (S P,S)-4-[( )-Menthylphenylphosphoryl]-1-(p-chlorophenyl)-4-(o-nitrophenyl)propan-2-one, 3m 31 P-NMR spectroscopy of crude 3m/3m =97:3 31 P-NMR spectroscopy of isolated 3m 33
34 1 H-NMR spectroscopy of isolated 3m 13 C-NMR spectroscopy of isolated 3m 34
35 (S P,S)-4-[( )-Menthylphenylphosphoryl]-1-(p-chlorophenyl)-4-(p-nitrophenyl)propan-2-one, 3n 31 P-NMR spectroscopy of crude 3n/3n =91:9 31 P-NMR spectroscopy of isolated 3n 35
36 1 H-NMR spectroscopy of isolated 3n 13 C-NMR spectroscopy of isolated 3n 36
37 (S P,R)-4-[( )-Menthylphenylphosphoryl]-1-(p-bromophenyl)-4-(p-diphenylaminephenyl)prop an-2-one, 3o 31 P-NMR spectroscopy of crude 3o/3o =58:42 31 P-NMR spectroscopy of isolated 3o/3o =4:96 37
38 1 H-NMR spectroscopy of isolated 3o/3o =4:96 13 C-NMR spectroscopy of isolated 3o/3o =4:96 38
39 (S P )-4-[( )-Menthylphenylphosphoryl]-1-phenyl-4-(2,6-dichlorophenyl)propan-2-one, 3p/3p 31 P-NMR spectroscopy of crude 3p/3p =65:35 31 P-NMR spectroscopy of isolated 3p/3p =60:40 39
40 1 H-NMR spectroscopy of isolated 3p/3p =60:40 13 C-NMR spectroscopy of isolated 3p/3p =60:40 40
41 (S P )-4-[( )-Menthylphenylphosphoryl]-1-phenyl-4-(2,4,6-trimethoxyphenyl)propan-2-one, 3q/3q 31 P-NMR spectroscopy of crude 3q/3q =64:36 31 P-NMR spectroscopy of isolated 3q/3q =62:
42 H-NMR spectroscopy of isolated 3q/3q =62:38 13 C-NMR spectroscopy of isolated 3q/3q =62:38 42
43 (S P )-4-[( )-Menthylphenylphosphoryl]-1-phenyl-4-(2,4,6-trimethylphenyl)propan-2-one, 3r/3r 31 P-NMR spectroscopy of crude 3r/3r =83:17 31 P-NMR spectroscopy of isolated 3r/3r =88:12 43
44 1 H-NMR spectroscopy of isolated 3r/3r =88:12 13 C-NMR spectroscopy of isolated 3r/3r =88:12 44
45 (S P,S)-4-[( )-Menthylphenylphosphoryl]-1-phenyl-4-(o-methoxynaphthyl)propan-2-one, 3s 31 P-NMR spectroscopy of crude 3s/3s =89:11 31 P-NMR spectroscopy of isolated 3s 45
46 1 H-NMR spectroscopy of isolated 3s 13 C-NMR spectroscopy of isolated 3s 46
47 (S P,S)-4-[( )-Menthylphenylphosphoryl]-1-phenyl-4-ferrocenecarboxpropan-2-one, 3t 31 P-NMR spectroscopy of crude 3t/3t =76:24 31 P-NMR spectroscopy of isolated 3t 47
48 1 H-NMR spectroscopy of isolated 3t 13 C-NMR spectroscopy of isolated 3t 48
49 (S P )-4-[( )-Menthylphenylphosphoryl]-pentan-3-one, 3u 31 P-NMR spectroscopy of crude 3u 31 P-NMR spectroscopy of isolated 3u 49
50 1 H-NMR spectroscopy of isolated 3u 13 C-NMR spectroscopy of isolated 3u 50
51 (S P,S)-4-[( )-Menthylphenylphosphoryl]-1-(p-bromophenyl)-4-(N-hexylphenothiazin)propan -2-one, 3v 31 P-NMR spectroscopy of crude 3v/3v =85:15 31 P-NMR spectroscopy of isolated 3v 51
52 1 H-NMR spectroscopy of isolated 3v 13 C-NMR spectroscopy of isolated 3v 52
53 (S P,S)-2-[( )-Menthylphenylphosphoryl]-2-phenyl-1H-indene-1,3(2H)-dione, 3w 31 P-NMR spectroscopy of crude 3w/3w =67:33 31 P-NMR spectroscopy of isolated 3w 53
54 1 H-NMR spectroscopy of isolated 3w 13 C-NMR spectroscopy of isolated 3w 54
55 (S P,R)-4-[( )-Menthylphenylphosphoryl]-1-pyridyl-4- pyridylpropan-2-one, 3x 31 P-NMR spectroscopy of crude 3x/3x =43:57 31 P-NMR spectroscopy of isolated 3x/3x =3:97 55
56 1 H-NMR spectroscopy of isolated 3x/3x =3:97 13 C-NMR spectroscopy of isolated 3x/3x =3:97 56
57 Methyl (S P )-3-[( )-Menthylphenylphosphoryl]propanoate, 5a 31 P-NMR spectroscopy of crude 5a 31 P-NMR spectroscopy of isolated 5a 57
58 1 H-NMR spectroscopy of isolated 5a 13 C-NMR spectroscopy of isolated 5a 58
59 Methyl (S P )-3-[( )-Menthylphenylphosphoryl]-3-phenylpropanoate, 5b 31 P-NMR spectroscopy of crude 5b/5b =83:17 31 P-NMR spectroscopy of isolated 5b 59
60 1 H-NMR spectroscopy of isolated 5b 13 C-NMR spectroscopy of isolated 5b 60
61 (S P,R)-4-[( )-Menthylphenylphosphoryl]-4-chroman-2-one, 5c 31 P-NMR spectroscopy of crude 5c/5c =43:57 31 P-NMR spectroscopy of isolated 5c 61
62 1 H-NMR spectroscopy of isolated 5c 13 C-NMR spectroscopy of isolated 5c 62
63 (S P )-[( )-Menthylphenylphosphoryl]propanenitrile, 5d 31 P-NMR spectroscopy of crude 5d 31 P-NMR spectroscopy of isolated 5d 63
64 1 H-NMR spectroscopy of isolated 5d 13 C-NMR spectroscopy of isolated 5d 64
65 (S P, 2R,3S)-3-[( )-Menthylphenylphosphoryl]-2-phenyl-3-(p-chlorophenyl)propanenitrile, 5e 31 P-NMR spectroscopy of crude product, the ratio of four stereomers: 22:13:61:4 31 P-NMR spectroscopy of isolated 5e 65
66 1 H-NMR spectroscopy of isolated 5e 13 C-NMR spectroscopy of isolated 5e 66
67 (S P,S)-( )-Menthylphenyl-2-nitro-1-phenylethyl phosphine oxide, 5f 31 P-NMR spectroscopy of crude 5f /5f =81:19 1 H-NMR spectroscopy of crude 5f/5f =81:19 67
68 31 P-NMR spectroscopy of isolated 5f 1 H-NMR spectroscopy of isolated 5f 68
69 13 C-NMR spectroscopy of isolated 5f 69
70 (S P,S)-( )-Menthylphenyl-2-nitro-1-p-methylphenylethyl phosphine oxide, 5g 31 P-NMR spectroscopy of crude 5g/5g =80:20 1 H-NMR spectroscopy of crude 5g/5g =80:
71 31 P-NMR spectroscopy of isolated 5g 1 H-NMR spectroscopy of isolated 5g 71
72 13 C-NMR spectroscopy of isolated 5g 72
73 (S P,S)-( )-Menthylphenyl-2-nitro-1-p-chlorophenylethyl phosphine oxide, 5h 31 P-NMR spectroscopy of crude 5h/5h =79:21 1 H-NMR spectroscopy of crude 5h/5h =79:21 73
74 31 P-NMR spectroscopy of isolated 5h 1 H-NMR spectroscopy of isolated 5h 74
75 13 C-NMR spectroscopy of isolated 5h 75
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Supplementary Figure 1. 1 H and 13 C NMR spectra for compound 1a
216.29 185.02 164.20 148.97 128.19 87.70 79.67 77.30 77.04 76.79 74.66 26.23 2.02 2.03 2.01 3.05 7.26 6.92 6.90 6.25 6.23 5.61 5.60 5.58 5.25 5.24 1.58 Supplementary Figure 1. 1 H and 13 C NMR spectra
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