First DMAP-mediated direct conversion of Morita Baylis. Hillman alcohols into γ-ketoallylphosphonates: Synthesis of

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1 Supporting Information File 1 for First DMAP-mediated direct conversion of Morita Baylis Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates Marwa Ayadi 1,2, Haitham Elleuch 1, Emmanuel Vrancken 2, and Farhat Rezgui* 1 Address: 1 Université de Tunis El Manar, Faculté des Sciences de Tunis, Laboratoire de Chimie Organique Structurale LR99ES14, Campus Universitaire, 2092 Tunis, Tunisie and 2 Institut Charles Gerhardt UMR 5253 CNRS-UM-ENSCM, 8 rue de l Ecole Normale Montpellier Cedex 5, France. Farhat Rezgui* - rez_far@yahoo.fr *Corresponding author Experimental procedures and characterization for synthesized compounds Table of contents: Analytical data...pages S2 S6 S1

2 Analytical data Materials and methods 1 H NMR and 13 C NMR spectra were recorded on a 300 MHz for 1 H and 75 MHz for 13 C in CDCl 3, using TMS as an internal standard (chemical shifts in δ values, J in Hz). 31 P NMR spectra were recorded on a 121 MHz using 85% H 3 PO 4 as an internal standard. High resolution mass spectra (HRMS) were recorded as TOF-HRMS on a micro mass spectrometer. Analytical thin layer chromatography (TLC) was performed using silica gel 60 F254 precoated silica gel plates. Visualization was achieved by UV light (254 nm). Flash chromatography was performed using silica gel 60. General method for the addition of trialkyl phosphite to acyclic MBH alcohols 3 A mixture of alcohol 3 (1 mmol) and trialkyl phosphite (2 mmol) was heated at 80 C. After the reaction was finished, the reaction mixture was cooled and the crude product was purified by flash chromatography on silica gel (diethyl ether/methylene chloride = 8:2) to give the corresponding phosphonates 4a f. Ethyl 2-(diphenoxyphosphoryl)methyl acrylate (4c) Yellow oil (215 mg, 62% yield). IR (FT-IR) 1735, 1598, 1497, 1295, 1204, 939, 766 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 10H), 6.43 (d, J = 6.0 Hz, 1H), 5.96 (d, J = 6.0 Hz, 1H), (m, 2H), 3.29 (d, J H-P = 21.0 Hz, 2H), (m, 3H); 13 C NMR (75 MHz, CDCl 3 ) δ (d, 3 J C-P = 6.7 Hz), (d, 2 J C-P = 9.0 Hz), (d, 2 J C-P = 10.5 Hz), 129.3, (d, 3 J C-P = 9.7 Hz), (d, 4 J C-P = 0.7 Hz, 2C), (d, 3 J C-P = 4.5 Hz, 2C), 61.4, 29.2 (d, 1 J C-P = Hz), 14.1; 31 P NMR (121 MHz, CDCl 3 ) δ 18.0; HRMS (ESI+) m/z calcd for [C 18 H 19 PO 5 +H] , found Reduction of γ-ketophosphonate 2a A mixture of γ-ketophosphonate 2a (5 mmol) and CeCl 3 6H 2 O (5 mmol) in methanol was stirred at 0 C. NaBH 4 (5 mmol) was thereafter added and the mixture was stirred at 0 C for S2

3 15 minutes then half an hour at room temperature. After completion, the reaction was neutralized with 2 M aqueous HCl solution and extracted with CH 2 Cl 2.the combined organic layers were dried over MgSO 4 and concentrated under vacuum. The crude product was chromatographed on a silica gel column using ether/ch 2 Cl 2 as eluent. Diethyl (6-hydroxycyclohex-1-en-1-yl)methylphosphonate (5) Pale yellow oil (1092mg, 88% yield). IR (FT-IR) 3413, 2951, 1235, 1056, 1040, 962 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 1H), (m, 5H), 2.78 (dd, J = 15.0, 21.0 Hz, 1H), 2.54 (dd, J = 15.0, 21.0 Hz, 1H), 2.04 (m, 2H), (m, 3H), 1.56 (s, 1H), (m, 7H); 13 C NMR (75 MHz, CDCl 3 ) δ (d, 3 J C-P = 10.5 Hz), (d, 2 J C-P = 10.5 Hz), 67.3, 62.5 (d, 2 J C-P = 6.7 Hz), 62.0 (d, 2 J C-P = 6.7 Hz), 32.5 (d, 1 J C-P = Hz), 31.5, 25.7 (d, 4 J C-P = 2.2Hz), 18.1, 16.4 (d, 3 J C-P = 3.0 Hz), 16.3 (d, 3 J C-P = 3.0 Hz); 31 P NMR (121MHz, CDCl 3 ) δ 29.8; HRMS (ESI+) m/z calcd for [C 11 H 21 PO 4 +Na] , found General method for the preparation of γ-tosylaminophosphonates 6 MBH alcohol 5 (1 mmol) was taken in CH 2 Cl 2 (5 ml) and I 2 (15 mol %) was added. The mixture was kept at room temperature. Sulfonamide (1.2 mmol) and 0.15 g of MgSO 4 were subsequently added and the mixture was stirred at 40 C. The reaction was monitored by TLC. After completion, the reaction was quenched with water (10 ml) and the mixture was extracted with methylene chloride. The extract was dried and concentrated and the residue was subjected to column chromatography (ether/petroleum ether) to obtain the pure γ- tosylaminophosphonates 6a d. Diethyl ((6-(phenylsulfonamido)cyclohex-1-en-1-yl)methyl)phosphonate (6a) Pale yellow crystal (267mg, 69% yield, mp 93 C). IR (FT-IR) 3126, 2954, , 1326, 1237, 1148, 1013, 962 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 2H), (m, 3H), 6.54 (d, J = 9.0 Hz, 1H), (m, 1H), (m, 4H), (m, 1H), (m, 1H), (m, 4H), (m, 3H), (m, 6H); 13 C NMR (75 MHz, CDCl 3 ) δ 140.5, (d, 3 J C-P = 9.7 Hz), 131.7, 128.3, 126.5, (d, 2 J C-P = 10.5 Hz), 61.9 (d, 2 J C-P = 7.5 Hz), 61.4 (d, 2 J C-P = 6.7 Hz), 51.7 (d, 3 J C-P = 3.0 Hz), 30.0, 30.2 (d, 1 J C-P = Hz), 24.7 (d, 4 J C-P = 3.0 Hz), 17.1, 15.8 (d, 3 J C-P = 5.2 Hz), 15.8 (d, 3 J C-P = 6.7 Hz); 31 P NMR (121 MHz, CDCl 3 ) δ 28.8; HRMS (ESI+) m/z calcd for [C 17 H 26 NO 5 PS+H] , found S3

4 Diethyl ((6-(4-methylphenylsulfonamido)cyclohex-1-en-1-yl)methyl)phosphonate (6b) Pale yellow crystal (253mg, 63% yield, mp 96 C). IR (FT-IR) 3126, 2947, 1333, 1237, 1148, 1029 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ) δ 7.83 (d, J = 6.0 Hz, 2H), 7.29 (d, J = 6.0 Hz, 2H), 6.35 (d, J = 6.0 Hz, 1H), (m, 1H), (m, 4H), (m, 1H), (m, 5H), (m, 4H), (m, 2H), (m, 6H); 13 C NMR (75 MHz, CDCl 3 ) δ 142.8, 138.1, (d, 3 J C-P = 10.5 Hz), , , (d, 2 J C-P = 10.5 Hz), 62.4 (d, 2 J C-P = 6.7 Hz), 61.9(d, 2 J C-P = 6.7 Hz), 52.2 (d, 3 J C-P = 3.0 Hz), 30.8 (d, 1 J C-p = Hz), 30.58, 25.2 (d, 4 J C-P = 3.0 Hz), 21.4, 17.71, 16.4 (d, 3 J C-P = 6.0 Hz), 16.3 (d, 3 J C-P =6.0 Hz); 31 P NMR (121 MHz, CDCl 3 ) δ 28.5; HRMS (ESI+) m/z calcd for [C 18 H 28 NO 5 PS+H] , found Diethyl ((6-(4-bromophenylsulfonamido)cyclohex-1-en-1-yl)methyl)phosphonate (6c) Pale yellow crystal (317mg, 68% yield, mp 92 C). IR (FT-IR) 3110, 2954, 1333, 1229, 1148, 1036, 962 cm -1 ; 1 H RMN (300 MHz, CDCl 3 ) δ 7.82 (d, J = 9.0 Hz, 2H), 7.63 (d, J = 9.0 Hz, 2H), 6.66 (d, J = 9.0 Hz, 1H), (m, 1H), (m, 4H), (m, 1H), 2.46 (dd, J = 15.0, 24.0 Hz, 1H), (m, 4H), (m, 3H), (m, 6H); 13 C NMR (75 MHz, CDCl 3 ) δ 140.4, (d, 3 J C-P = 9.75 Hz), 132.1, 128.8, 127.0, (d, 2 J C-P = 10.5 Hz), 62.6 (d, 2 J C-P = 6.7 Hz), 62.1 (d, 2 J C-P = 6.7 Hz), 52.6 (d, 3 J C-P = 3.0 Hz), 32.1 (d, 1 J C-P = Hz), 30.8, 25.3 (d, 4 J C-P = 3.7 Hz), 17.8, 16.5 (d, 3 J C-P = 6.7 Hz), 16.4 (d, 3 J C-P = 6.0 Hz); 31 P NMR (121 MHz, CDCl 3 ) δ 28.9; HRMS (ESI+) m/z calcd for [C 17 H 25 BrNO 5 PS+H] , found Diethyl ((6-(N,4-dimethylphenylsulfonamido)cyclohex-1-en-1-yl)methyl)phosphonate (6d) Brown oil (291mg, 70% yield). IR (FT-IR) 2954, 1341, 1252, 1162, 1043, 962, 664, 553 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ) δ 7.74 (d, J = 9.0 Hz, 2H), 7.30 (d, J = 9.0 Hz, 2H), (m, 1H), (m, 1H), (m, 4H), 2.64 (s, 3H), 2.42 (s, 3H), 2.37 (d, J = 21.0 Hz, 2H, H-7), (m, 2H), (m, 4H), (m, 6H); 13 C NMR (75 MHz, CDCl 3 ) δ 143.1, 137.0, (d, J C-P = 9.7 Hz), 129.6, 127.2, (d, 2 J C-P = 9.7 Hz), 61.9 (d, 2 J C-P = 2.2 Hz), 61.8 ( d, 2 J C-P = 2.2 Hz), 55.8 (d, 3 J C-P = 5.2 Hz), 28.8 (d, 1 J C-P = Hz), 29.6, 26.7, 25.0 (d, 4 J C-P = 2.2 Hz), 21.5, 20.2, 16.4 (d, 3 J C-P = 6.0 Hz,); 31 P NMR (121 MHz, CDCl 3 ) δ 27.8; HRMS (ESI+) m/z calcd for [C 19 H 30 NO 5 PS+H] , found S4

5 Acetylation of γ-hydroxyphosphonate 5 2-((Diethoxyphosphoryl)methyl)cyclohex-2-en-1-yl acetate (7) [1] Colorless oil (1305 mg, 90% yield). IR (FT-IR) 2954, 1750, 1252, 1036, 962 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ) δ 5.93 (t, J = 3 Hz, 1H), (m, 1H), (m, 4H), (m, 2H), 2.02 (s, 3H), (m, 2H), (m, 2H), (m, 2H), (m, 6H); 13 C NMR (75 MHz, CDCl 3 ) δ 170.6, (d, 2 J C-P = 11.2 Hz), (d, 3 J C-P = 10.5 Hz), 69.3 (d, 3 J C-P = 3.0 Hz), 61.8 (d, 2 J C-P = 6.7 Hz), 61.6 (d, 2 J C-P = 6.7 Hz), 30.9 (d, 1 J C-P = Hz), 28.5, 25.2 (d, 4 J C-P = 3.0 Hz), 21.2, 17.6, 16.3 (d, 3 J C-P = 6.0 Hz); 31 P NMR (121 MHz, CDCl 3 ) δ 27.4; HRMS (ESI+) m/z calcd for [C 13 H 23 PO 5 +Na] , found General method for the preparation of γ-aminophosphonates 8 MBH acetate 7 (1 mmol) and CeCl 3.6H 2 O (1 mmol) was taken in 5 ml of toluene. The mixture was kept at room temperature. Aromatic amine (1.2 mmol) was added and the mixture was stirred at 110 C. The reaction was monitored by TLC. After completion, the reaction was quenched with water and the mixture was extracted with methylene chloride. The extract was dried, concentrated and the residue was subjected to column chromatography on silica gel (ether / petroleum ether) to obtain pure γ-aminophosphonates 8a-e. Diethyl (6-(phenylamino) cyclohex-1-en-1-yl)methylphosphonate (8a) Yellow oil (194 mg, 60% yield). IR (FT-IR) 3349, 2947, 1616, 1505, 1244, 1036, 969 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 2H), (m, 3H), (m, 1H), 4.33 (s, 1H), (m, 5H), 2.74 (dd, J= 15.0, 21.0 Hz, 1H), 2.55 (dd, J= 15.0, 21.0 Hz, 1H), (m, 2H), (m, 4H), (m, 6H); 13 C NMR (75 MHz, CDCl 3 ) δ 147.7, (d, 3 J C-P = 11.2 Hz), 129.2, (d, 2 J C-P = 9.7 Hz), 116.7, 112.9, 61.9 (d, 2 J C-P = 6.0 Hz), 61.8 (d, 2 J C-P = 5.0 Hz), 50.4 (d, 3 J C-P = 3.0 Hz), 31.5 (d, 1 J C-P = Hz), 28.18, 25.5 (d, 4 J C-P = 3.0 Hz), 17.8, 16.5 (d, 3 J C-P = 3.0 Hz), 16.4 (d, 3 J C-P = 3.0 Hz); 31 P NMR (121 MHz, CDCl 3 ) δ 28.6; HRMS (ESI+) m/z calcd for [C 17 H 26 NO 3 P+H] , found Diethyl (6-((4-nitrophenyl) amino) cyclohex-1-en-1-yl)methylphosphonate (8b) Yellow crystal (298 mg, 81% yield, mp 107 C). IR (FT-IR) 3282, 2947, 1608, 1475, 1326, 1237, 1110 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ) δ 8.05 (d, J = 9.0 Hz, 2H), 6.60 (d, J = 9.0 Hz, 2H), 6.14 (d, S5

6 J = 9.0 Hz, 1H), (m, 1H), (m, 5H), 2.71 (dd, J = 15.0, 24.0 Hz, 1H), 2.41 (dd, J = 15.0, 18.0 Hz, 1H), (m, 2H), (m, 2H), (m, 2H), (m, 6H); 13 C NMR (75 MHz, CDCl 3 ) δ 153.1, 137.1, (d, 2 J C-P = 11.2 Hz), (d, 3 J C-P = 11.2 Hz), 126.3, 110.9, 62.2 (d, 2 J C-P = 7.5 Hz), 62.0 (d, 2 J C-P = 6.7 Hz), 51.0 (d, 3 J C-P = 2.2), 31.5 (d, 1 J C-P = Hz), 28.34, (d, 4 J C-P = 3.0 Hz), 18.09, 16.3 (d, 3 J C-P = 6.0 Hz), 16.2 (d, 3 J C-P = 6.0 Hz); ); 31 P NMR (121 MHz, CDCl 3 ) δ 28.7; HRMS (ESI+) m/z calcd for [C 17 H 25 N 2 O 5 P+H] , found Diethyl (6-((4-fluorophenyl) amino)cyclohex-1-en-1-yl)methylphosphonate (8c) Yellow oil (225 mg, 66% yield). IR (FT-IR) 3333, 2947, 1512, 1229, 1029, 969 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 2H), (m, 2H), 5.85 (t, J = 3 Hz, 1H), (m, 5H), 2.75 (dd, J = 15 Hz, 1H), 2.45 (dd, J = 15 Hz, 1H), (m, 2H), ( m, 2H), (m, 2H), (m, 6H) ; 13 C NMR (75 MHz, CDCl 3 ) δ (d, 1 J C-F = Hz), (d, 4 J C-F = 1.8 Hz), (d, 3 J C-P = 11.0 Hz), (d, 2 J C-P = 10.4 Hz), (d, 2 J C-F = 22.2 Hz), (d, 3 J C-F = 7.2 Hz), 61.8 (d, 2 J C-P = 6.0 Hz), 61.7 (d, 2 J C-P = 6.0 Hz), 51.6 (d, 3 J C-P = 3.1 Hz), 31.7 (d, 1 J C-P = Hz), 28.4, 25.5 (d, 4 J C-P = 2.9 Hz), 17.9, 16.3 (d, 3 J C-P = 2.1 Hz), 16.2 (d, 3 J C-P = 2.1 Hz); 31 P NMR (121 MHz, CDCl 3 ) δ 28.2; 19 F NMR (300 MHz, CDCl 3 ) δ (m); HRMS (ESI+) m/z calcd for [C 17 H 25 FNO 3 P+H] , found Diethyl (6-(naphthalen-2-ylamino) cyclohex-1-en-1-yl)methylphosphonate (8d) Yellow oil (149 mg, 40% yield). IR (FT-IR) 3378, 2947, 1594, 1542, 1415, 1237, 1029, 984, 783 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ) δ (m, 1H), (m, 1H), (m, 4H), 6.66 (d, J = 7.6 Hz, 1H), 5.96 (t, J = 3 Hz, 1H), (m, 5H), 2.77 (dd, J = 22.3, 15.1 Hz, 1H), 2.56 (dd, J = 20.7, 15.1 Hz, 1H), (m, 3H), (m, 1H), (m, 2H), (m, 6H); 13 C NMR (75 MHz, CDCl 3 ) δ 143.0, 134.9, (d, 3 J C-P = 10.8 Hz), (d, 2 J C-P = 10.5 Hz), 128.5, 126.6, 125.6, 124.5), 123.9, 120.8, 116.7, 104.2, 62.0 (d, 2 J C-P = 6.6 Hz), 61.9 (d, 2 J C-P = 6.9 Hz), 51.1 (d, 3 J C-P = 3.2 Hz), 31.8 (d, 1 J C-P = Hz), 28.2, 25.8 (d, 4 J C-P = 3.0 Hz), 18.7, 16.4 (d, 3 J C-P = 5.8 Hz, 16.4 (d, 3 J C-P = 5.6 Hz); 31 P NMR (121 MHz, CDCl 3 ) δ 28.6; HRMS (ESI+) m/z calcd for [C 21 H 28 NO 3 P+H] , found S6

7 Reference 1. Rezgui, F.; El Gaïed, M. M. J. Chem. Res., Synop. 1999, doi: /a902012h S7

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