Department of Chemistry and Biochemistry, California State University Northridge, Northridge, CA Experimental Procedures
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1 Supporting Information Low Temperature n-butyllithium-induced [3,3]-Sigmatropic Rearrangement/Electrophile Trapping Reactions of Allyl-1,1- Dichlorovinyl Ethers. Synthesis of - - and -lactones. Aaron Christopher a, Dahniel Brandes a, Stephen Kelly a and Thomas G. Minehan* a Department of Chemistry and Biochemistry, California State University Northridge, Northridge, CA Experimental Procedures pp. S1 Spectroscopic data for compounds: 2a, 2e, 2h, 2j, 3a-3j, 3l-3r, 4f pp. S2-S22 IR spectra for compounds 3j, 3n, and 3p pp. S23-S25 1 HNMR and 13 CNMR spectra for compounds: 2a, 2e, 2h, 2j, 3a-3j, 3l-3r, 4f pp. S26-S46 S0
2 General Methods. Distilled water was used in all of the experiments. rganic extracts were dried over Na 2 S 4, filtered, and concentrated using a rotary evaporator at aspirator pressure (20-30mmHg). Chromatography refers to flash chromatography and was carried out on Si 2 (silica gel 60, mesh). 1 H and 13 C NMR spectra were measured in CDCl 3 at 400 MHz and 100 MHz, respectively, using Me 4 Si as internal standard. Chemical shifts are reported in ppm downfield ( ) from Me 4 Si. A. General procedure for [3,3] sigmatropic rearrangement/ketone trapping of allyl-1,1- dichlorovinyl ethers to form -lactones 3a-3j. The allyl-1,1-dichlorovinyl ether 2a (188 mg, 0.85 mmol) was dissolved in THF (5 ml) and cooled to -78 C. n-buli (1.27 ml, 2M in cyclohexane, 2.54 mmol, 3 equivalents) was added dropwise at -78 C and the dark-colored solution was stirred at this temperature for 45 minutes. Then the ketone (1.7 mmol, 2 equivalents) was added and the mixture was stirred at -78 C for another 45 minutes. A solution of saturated NaHC 3 (5 ml) was added, followed by ether (5 ml) and the mixture was allowed to warm to room temperature. The phases were separated and the aqueous layer was further extracted with ether (2 x 25 ml). The combined organic extracts were once washed with 20 ml sat. aq. NaCl, dried over anhydrous Na 2 S 4 and concentrated under reduced pressure to give a crude oil. Purification of the residue by flash chromatography afforded -lactones 3. B. General procedure for [3,3] sigmatropic rearrangement/ketone trapping of allyl-1,1- dichlorovinyl ethers to form and -lactones 3l-3r. The allyl-1,1-dichlorovinyl ether 2a (188 mg, 0.85 mmol) was dissolved in THF (5 ml) and cooled to -78 C. n-buli (1.27 ml, 2M in cyclohexane, 2.54 mmol, 3 equivalents) was added dropwise at -78 C and the dark-colored solution was stirred at this temperature for 45 minutes. Then the epoxide or oxetane (1.7 mmol, 2 equivalents) was added, followed by BF 3 Et 2 (1.7 mmol, 2 equivalents) and the mixture was stirred at -78 C for another 45 minutes. A solution of saturated NaHC 3 (5 ml) was added, followed by ether (5 ml) and the mixture was allowed to warm to room temperature. The phases were separated and the aqueous layer was further extracted with ether (2 x 25 ml). The combined organic extracts were once washed with 20 ml sat. aq. NaCl, dried over anhydrous Na 2 S 4 and concentrated under reduced pressure to give a crude oil. Purification of the residue by flash chromatography afforded - or lactones 3. S1
3 Cl Cl 2a Compound 2a was prepared from 1-octene-2-ol in 68% overall yield according to the procedure in main text reference 4. See spectra on page S24 1 H NMR: (400 MHz, CDCl 3 ) 6.55 (s, 1H); 5.77 (m, 1H); 5.28 (d, J=5.2 Hz, 1H); 5.24 (s, 1H); 4.12 (q, J=6.8 Hz, 1H); 1.73 (m, 1H); 1.59 (m, 1H); (m, 6H); 0.91 (t, J=6.4 Hz, 3H). 13 C NMR: (100 MHz, CDCl 3 ) 141.8; 137.1; 118.1; 103.9; 84.7; 34.7; 31.5; 24.6; 22.6; 22.4; HRMS (ESI): calculated for C 10 H 17 Cl , found (M+H) + MS spectra were difficult to obtain because dichlorovinyl ethers undergo facile [3,3] sigmatropic rearrangement reactions upon exposure to thermal, ionizing or acidic conditions (rg Lett. 2006, 8, 451). As a result, the [M+H] + and [M+Na] + signals for dichlorovinyl ethers 2a, 2e, 2h and 2j are very weak. The thermal rearrangement of allyl-1,1-dichlorovinyl ethers is known (Synthesis 1981, 308). S2
4 Cl 2e Cl Compound 2e was prepared from 2-cyclohexylideneethanol a according to the procedure in main text reference 4. in 51% overall yield See spectra on page S25 1 H NMR: (400 MHz, CDCl 3 ) 6.55 (s, 1H); 5.32 (t, J=6.2 Hz, 1H); 4.42 (s, 1H); 4.40 (s, 1H); 2.22 (m, 2H); 2.16 (m, 1H); 1.73 (m, 2H); 1.58 (m, 4H). 13 C NMR: (100 MHz, CDCl 3 ) 148.0; 143.3; 142.5; 115.5; 72.0; 68.7; 37.0; 34.2; 33.1; 29.1; 28.3; 27.7; 26.5; 26.4; HRMS (ESI): calculated for C 10 H 14 Cl 2 Na , found (M+H) + a Koo, J.; Park, H.-S; Shin, S. Tetrahedron Lett. 2013, 54, 834. S3
5 Cl 2h Cl Compound 2h was prepared from 2-cyclopentylideneethanol b according to the procedure in main text reference 4. in 62% overall yield See spectra on page S26 1 H NMR: (400 MHz, CDCl 3 ) 6.55 (s, 1H); 5.47 (m, 1H); 4.39 (s, 1H); 4.37 (s, 1H); 2.34 (t, J=7.0 Hz, 2H); 2.27 (t, J=7.4 Hz, 2H); 1.66 (m, 4H). 13 C NMR: (100 MHz, CDCl 3 ) 151.5; 142.7; 114.4; 71.1; 33.8; 29.0; 26.2; HRMS (ESI): calculated for C 9 H 13 Cl , found (M+H) + b Rigoli, J.W.; Moyer, S.A.; Pearce, S.D.; Schomaker, J.M. rg. Biomol. Chem. 2012, 10, S4
6 Cl 2j Cl CH 3 Compound 2j was prepared from 2-cyclohexylidenepropan-1-ol c in 90% overall yield according to the procedure in main text reference 4. See spectra on page S27 1 H NMR: (400 MHz, CDCl 3 ) 6.51 (s, 1H); 4.43 (s, 2H); 2.25 (m, 4H); 1.74 (s, 3H); 1.57 (m, 6H). 13 C NMR: (100 MHz, CDCl 3 ) 142.3; 141.3; 119.9; 104.6; 73.1; 30.9; 30.4; 28.4; 27.8; 26.6; HRMS (ESI): calculated for C 11 H 16 Cl 2 Na , found (M+Na) + c Kuroda, C.; Koshio, H; Koito, A.; Sumiya, H.; Murase, A.; Hirono, Y. Tetrahedron 2000, 56, S5
7 3a Compound 3a was prepared from 2a in 70% yield according to general procedure A outlined above. See spectra on page S28 1 H NMR: (400 MHz, CDCl 3 ) 5.52 (m, 1H); 5.39 (m, 1H); 3.54 (dd, J=9.6, 6.3 Hz, 2H); 2.52 (m, 1H); 2.41 (m, 1H); 2.15 (m, 1H); (m, 8H); (m, 6H); 0.91 (t, J=6.8 Hz, 3H). 13 C NMR: (100 MHz, CDCl 3 ) 171.3; 133.5; 125.0; 91.3; 54.4; 37.8; 32.4; 32.0; 31.3; 28.9; 28.8; 23.5; 23.4; 22.4; HRMS (ESI): calculated for C 15 H , found (M+H) + S6
8 3b Compound 3b was prepared from 2a in 56% yield according to general procedure A outlined above. See spectra on page S29 1 H NMR: (400 MHz, CDCl 3 ) 5.51 (m, 1H); 5.42 (m, 1H); 3.19 (t, J=6.7 Hz, 2H); 2.48 (m, 2H); 2.04 (q, J=6.9 Hz, 2H);1.94 (m, 1H); (m, 10H); (m, 8H); 0.93 (t, J=4.0 Hz, 3H). 13 C NMR: (100 MHz, CDCl 3 ) 171.6; 133.4; 125.5; 82.4; 57.8; 37.4; 32.4; 31.4; 31.3; 31.1; 28.9; 27.0; 25.3; 24.9; 22.8; 22.7; 22.5; 22.4; 22.0; HRMS (ESI): calculated for C 16 H 26 Na , found (M+Na) + S7
9 3c Compound 3c was prepared from 2a in 85% yield according to the general procedure A outlined above. See spectra on page S30 1 H NMR: (400 MHz, CDCl 3 ) 5.54 (dt, J=15.2, 7.0 Hz, 1H); 5.38 (dt, J=13.5, 7.5 Hz, 1H); 3.27 (dd, J=9.5, 6.6 Hz, 2H); 2.50 (m, 1H); 2.41 (m, 1H); 2.03 (m, 2H); (m, 3H); (m, 9H); 1.00 (t, J=7.5 Hz, 3H); 0.94 (m, 6H). 13 C NMR: (100 MHz, CDCl 3 ) 171.5; 133.7; 125.6; 85.2; 56.8; 32.3; 31.3; 29.1; 28.9; 27.4; 24.5; 22.4; 14.0; 8.1; 7.3. HRMS (ESI): calculated for C 15 H 26 Na , found (M+Na) + S8
10 3d H 3 C Compound 3d was prepared from 2a in 71% yield according to the general procedure A outlined above. See spectra on page S31; product obtained as a mixture of diastereomers 1 H NMR: (400 MHz, CDCl 3 ) 7.36 (m, 5H); 5.22 (m, 2H); 3.59 (t, J=8.2 Hz, 1H); 1.97 (s, 3H); (m, 4H); 1.28 (m, 6H); 0.91 (t, J=6.7 Hz, 3H). 13 C NMR: (100 MHz, CDCl 3 ) 170.7; 138.8; 133.5; 128.3; 128.0; 125.3; 124.3; 82.3; 60.5; 32.3; 31.3; 29.3; 28.9; 27.7; 22.4; HRMS (ESI): calculated for C 18 H 24 Na , found (M+Na) + S9
11 Compound 3e was prepared from 2e in 81% yield according to the general procedure A outlined above. See spectra on page S32 1 H NMR: (400 MHz, CDCl 3 ) 5.81 (dd, J=17.8, 11.0, 1H); 5.30 (d, J=11.0 Hz, 1H); 5.20 (d, J=13.8 Hz, 1H); 3.23 (s, 1H); 2.21 (m, J=6.4 Hz, 1H); 2.07 (m, 1H); 2.01 (m, J=6.4 Hz, 1H); 1.84 (m, J=7.3 Hz, 1H); 1.72 (m, 1H); 1.55 (m, 8H); 1.26 (m, 1H); 0.93 (t, J=7.3 Hz, 3H); 0.89 (t, J=6.4 Hz, 3H). 13 C NMR: (100 MHz, CDCl 3 ) 170.5; 142.2; 116.4; 87.2; 67.7; 40.3; 34.9; 30.2; 25.7; 25.2; 21.9; 21.4; 8.3; 7.5. HRMS (ESI): calculated for C 15 H 24 Na , found (M+Na) + 3e S10
12 Compound 3f was prepared from 2e in 84% yield according to the general procedure A outlined above. 3f See spectra on page S33 1 H NMR: (400 MHz, CDCl 3 ) 5.84 (d, J=11.2 Hz, 1H); 5.79 (d, J=10.8 Hz, 1H); 5.24 (d, J=10.8 Hz, 1H); 5.17 (d, J=18.8 Hz, 1H); 3.56 (s, 1H); 2.08 (m, 2H); 1.98 (m, 1H); (m, 14H; 1.30 (m, 1H). 13 C NMR: (100 MHz, CDCl 3 ) 170.5; 141.6; 116.1; 91.5; 63.9; 40.3; 39.7; 34.4; 33.3; 33.2; 25.6; 23.9; 22.1; 21.8; HRMS (ESI): calculated for C 15 H 22 Na , found (M+Na) + S11
13 H 3 C 3g Compound 3g was prepared from 2e in 56% yield according to the general procedure A outlined above. See spectra on page S34; product obtained as a mixture of diastereomers 1 H NMR: (400 MHz, CDCl 3 ) (m, 5H); 5.28 (d, J=11 Hz, 1H); 5.23 (d, J=10.9 Hz, 1H); 5.06 (d, J=10.9 Hz, 1H); 4.88 (d, J=18.6 Hz, 1H); 3.64 (s, 1H); 1.92 (s, 3H); (m, 10H) 13 C NMR: (100 MHz, CDCl 3 ) 168.9; 141.1; 139.5; 128.0; 127.7; 126.7; 123.6; 115.8; 82.8; 71.9; 40.5; 35.6;34.6; 33.1; 32.6; 29.9; 26.1; 25.5; 22.0; 21.6; HRMS (ESI): calculated for C 18 H 22 Na , found (M+Na) + S12
14 Compound 3h was prepared from 2h in 62% yield according to the general procedure A outlined above. 3h See spectra on page S35 1 H NMR: (400 MHz, CDCl 3 ) 5.82 (d, J=10.7 Hz, 1H); 5.80 (d, J=10.7, Hz, 1H); 5.12 (d, J=10.7 Hz, 1H); 5.09 (d, J=8.6 Hz, 1H); 3.32 (s, 1H); 2.19 (m, 1H); 1.89 (m, 3H); 1.65 (m, 15H). 13 C NMR: (100 MHz, CDCl 3 ) 170.9; 142.9; 113.4; 84.1; 67.1; 48.0; 38.3; 36.1; 34.9; 31.6; 24.9; 23.1; 22.5; 21.6 HRMS (ESI): calculated for C 15 H 22 Na , found (M+Na) + S13
15 H 3 C H 3 C 3i Compound 3i was prepared from 2h in 91% yield according to general procedure A outlined above. See spectra on page S36; product obtained as a mixture of diastereomers 1 H NMR: (400 MHz, CDCl 3 ) 5.83 (m, 2H); (m, 4H); 5.52 (s, 1H); 3.49 (s, 1H); 2.02 (m, 1H); (m, 19H); 1.55 (s, 3H); 1.51 (s, 3H); 0.99 (q, J=7.4 Hz, 3H) 13 C NMR: (100 MHz, CDCl 3 ) 170.6; 170.4; 142.8; 142.5; 113.7; 113.3; 84.5; 84.2; 67.6; 65.0; 48.1; 37.5; 37.1; 35.1; 34.3; 28.0; 25.0; 24.6; 24.5; 22.5; 22.4; 19.7; 8.4; 7.8. HRMS (ESI): calculated for C 13 H 21 Na , found (M+Na) + S14
16 H 3 C H 3 C CH 3 3j Compound 3j was prepared from 2j in 93% yield according to general procedure A outlined above. See spectra on page S37 1 H NMR: (400 MHz, CDCl 3 ) 5.19 (s, 1H); 4.98 (s, 1H); 3.37 (s, 1H); 2.26 (m, 2H); 1.76 (s, 3H); (m, 3H); 1.60 (s, 3H); 1.58 (m, 3H); 1.49 (s, 3H); 1.25 (m, 2H) 13 C NMR: (100 MHz, CDCl 3 ) 170.8; 143.2; 116.1; 81.9; 65.7; 43.2; 34.2; 30.9; 29.7; 25.7; 22.6; 22.0; 21.6; IR: 1807, 1222, 1069, 899, 802 cm -1 HRMS (ESI): calculated for C 14 H 22 Na , found (M+Na) + S15
17 H 4f Compound 4f was prepared from 3f in >95% yield by the following procedure: Compound 3f (45 mg, 0.19 mmol) was dissolved in CH 2 Cl 2 (1 ml) and cooled to -78 C. Then allyltrimethylsilane (0.08 ml, 0.5 mmol) was added, followed by TMSTf (0.1 ml, 0.5 mmol). The reaction was stirred 10 minutes at -78 C and then saturated aqueous NaHC 3 solution (5 ml) and ether (5 ml) was added. The phases were separated and the aqueous layer was further extracted with ether (2 x 25 ml). The combined organic extracts were once washed with 20 ml sat. aq. NaCl, dried over anhydrous Na 2 S 4 and concentrated under reduced pressure to give a crude oil. 1 H NMR of the crude oil indicated that product 4f was >95% pure. See spectra on page S38 1 H NMR: (400 MHz, CDCl 3 ) 5.88 (dd, J=17.8, 11.0 Hz, 1H); 5.67 (m, 1H); 5.23 (d, J=11.0 Hz, 1H); 5.03 (d, J=17.8 Hz, 1H); 3.29 (s, 1H); 2.42 (m, 2H); 2.35 (m, 2H); 1.85 (m, 3H); (m, 9H). 13 C NMR: (100 MHz, CDCl 3 ) 178.4; 142.9; 137.9; 131.0; 115.1; 57.4; 42.7; 36.5; 34.5; 32.8; 30.3; 29.6; 26.1; 23.6; 22.1; HRMS (ESI): calculated for C 15 H 22 Na , found (M+Na) + S16
18 + Compounds 3l were prepared from 2a in 56% yield according to general procedure B outlined above. 3l See spectra on page S39; product obtained as a mixture of regioisomers 1 H NMR: (400 MHz, CDCl 3 ) 5.46 (dt, J=8.4, 0.8 Hz, 1H); 5.29 (dt, J=8.0, 6.8 Hz, 1H); 4.05 (m, 2H); 2.59 (m, 1H); 2.28 (m, 1H); 2.14 (m, 1H); (m, 2H); (m, 2H); (m, 6H); 1.20 (s, 3H); 1.19 (s, H); 0.92 (t, J=7.6 Hz, 3H) 13 C NMR: (100 MHz, CDCl 3 ) 177.0; 133.5; 126.2; 70.4; 64.3; 44.8; 41.6; 37.1; 32.4; 31.3; 30.6; 30.5; 29.0; 28.4; 22.5; 19.1; 14.0; HRMS (ESI): calculated for C 14 H , found (M+H) + S17
19 H H 3n Compound 3n was prepared from 2e in 78% yield according to general procedure B outlined above. See spectra on page S41; product obtained as a mixture of diastereomers 1 H NMR: (400 MHz, CDCl 3 ) 5.82 (dd, J=17.8, 11.0 Hz, 1H); 5.26 (d, J=11.0 Hz, 1H); 5.11 (d, J=17.8 Hz, 1H); 3.63 (td, J=10.7, 3.5 Hz, 1H); 2.36 (d, J=12.0 Hz, 1H); 2.17 (m, 3H); (m, 6H); (m, 7H); (m, 3H) 13 C NMR: (100 MHz, CDCl 3 ) 176.2; 142.5; 115.8; 81.9; 54.3; 45.7; 41.7; 34.2; 33.6; 30.6; 30.1; 26.1; 25.5; 23.9; 21.9; IR: 1770, 1080, 1035, 912 cm -1 HRMS (ESI): calculated for C 16 H 24 Na , found (M+Na) + S18
20 Compound 3o was prepared from 2e in 89% yield according to general procedure B outlined above. 3o See spectra on page S42: product obtained as a mixture of diastereomers 1 H NMR: (400 MHz, CDCl 3 ) 5.77 (dd, J=17.8, 11.0 Hz, 1H); 5.26 (dd, J=11.0, 1.2 Hz, 1H); 5.08 (dd, J=17.8, 1.3 Hz, 1H); 4.23 (m, 1H); 2.67 (dd, J=12.4, 8.6 Hz, 1H); 2.21 (m, 1H); 2.16 (m, 1H); (m, 10H); 0.92 (t, J=6.8 Hz, 3H). 13 C NMR: (100 MHz, CDCl 3 ) 176.4; 141.7; 116.1; 48.8; 40.8; 35.8; 35.1; 33.7; 33.2; 30.7; ; 26.0; 22.4; 21.9; 21.8; HRMS (ESI): calculated for C 16 H 26 Na , found (M+Na) + S19
21 Compound 3p was prepared from 2e in 65% yield according to general procedure B outlined above. 3p See spectra on page S43 1 H NMR: (400 MHz, CDCl 3 ) 5.83 (dd, J=17.8, 11.0 Hz, 1H); 5.26 (d, J=6.5, 1.3 Hz, 1H); 5.07 (d, J=17.8, 1.3 Hz, 1H); 3.86 (m, 2H); 2.60 (dd, J=10.8, 8.4 Hz, 1H); (m, 12H); 1.06 (s, 3H); 0.99 (s, 3H). 13 C NMR: (100 MHz, CDCl 3 ) 172.1; 142.1; 115.7; 70.1; 45.3; 42.4; 35.0; 35.4; 34.6; 32.4; 31.9; 30.6; 30.5; 28.5; 28.2; 26.8; 26.1; 24.0; 22.6; 22.1; 21.9; IR: 2927, 1727, , 1073, 914 cm -1 HRMS (ESI): calculated for C 15 H 24 Na , found (M+Na) + S20
22 H 3q Compound 3q was prepared from 2h in 71% yield according to general procedure B outlined above. See spectra on page S44: product obtained as a mixture of diastereomers 1 H NMR: (400 MHz, CDCl 3 ) 5.81 (dd, J=17.4, 10.7 Hz, 1H); 5.17 (d, J=10.7 Hz, 1H); 5.09 (d, J=17.5 Hz, 1H); 3.67 (td, J=14.7, 3.5 Hz, 1H); 2.28 (d, J=12.3 Hz, 1H); 2.19 (m, 1H); 1.91 (m, 2H); 1.78 (m, 2H); 1.65 (m, 4H); (m, 3H); (m, 4H). 13 C NMR: (100 MHz, CDCl 3 ) 176.4; 141.3; 114.7; 82.2; 56.3; 49.7; 47.1; 39.0; 37.0; 35.2; 30.1; 29.2; 25.3; 23.3; HRMS (ESI): calculated for C 15 H 242 Na , found (M+Na) + H S21
23 Compound 3r was prepared from 2j in 68% yield according to general procedure B outlined above. See spectra on page S45 1 H NMR: (400 MHz, CDCl 3 ) 5.15 (s, 1H); 4.86 (s, 1H); 4.29 (m, 1H); 4.16 (m, 1H); 2.56 (t, J=9.6 Hz, 1H); (m, 6H); 1.68 (s, 3H); (m, 5H); 1.27 (m, 3H). 13 C NMR: (100 MHz, CDCl 3 ) 172.3; 145.0; 115.8; 68.9; 46.6; 33.2; 31.3; 30.7; 26.0; 23.1; 22.4; 21.1; 22.0; HRMS (ESI): calculated for C 14 H 22 Na , found (M+Na) + CH 3 3r S22
24 H 3 C H 3 C CH 3 3j S23
25 H H 3n S24
26 3p S25
27 Cl Cl 2a 1 H (400 MHz) and 13 C NMR (100 MHz) spectra S26
28 Cl 2e Cl 1 H (400 MHz) and 13 C NMR (100 MHz) spectra S27
29 Cl 2h Cl 1 H (400 MHz) and 13 C NMR (100 MHz) spectra S28
30 Cl 2j Cl CH 3 1 H (400 MHz) and 13 C NMR (100 MHz) spectra S29
31 3a 1 H (400 MHz) and 13 C NMR (100 MHz) spectra S30
32 3b 1 H (400 MHz) and 13 C NMR (100 MHz) spectra S31
33 3c 1 H (400 MHz) and 13 C NMR (100 MHz) spectra S32
34 3d H 3 C 1 H (400 MHz) and 13 C NMR (100 MHz) spectra; product obtained as a mixture of diastereomers S33
35 3e 1 H (400 MHz) and 13 C NMR (100 MHz) spectra S34
36 3f 1 H (400 MHz) and 13 C NMR (100 MHz) spectra S35
37 H 3 C 3g 1 H (400 MHz) and 13 C NMR (100 MHz) spectra; product obtained as a mixture of diastereomers S36
38 3h 1 H (400 MHz) and 13 C NMR (100 MHz) spectra S37
39 H 3 C H 3 C 3i 1 H (400 MHz) and 13 C NMR (100 MHz) spectra product obtained as a mixture of diastereomers S38
40 H 3 C H 3 C CH 3 3j 1 H (400 MHz) and 13 C NMR (100 MHz) spectra S39
41 H 4f 1 H (400 MHz) and 13 C NMR (100 MHz) spectra S40
42 + 3l 1 H (400 MHz) and 13 C NMR (100 MHz) spectra product obtained as a mixture of regioisomers S41
43 H H 3n 1 H (400 MHz) and 13 C NMR (100 MHz) spectra product obtained as a mixture of diastereomers S42
44 3o 1 H (400 MHz) and 13 C NMR (100 MHz) spectra product obtained as a mixture of diastereomers S43
45 3p 1 H (400 MHz) and 13 C NMR (100 MHz) spectra S44
46 H H 3q 1 H (400 MHz) and 13 C NMR (100 MHz) spectra product obtained as a mixture of diastereomers S45
47 CH 3 1 H (400 MHz) and 13 C NMR (100 MHz) spectra 3r S46
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