Pentanidium catalyzed enantioselective phase transfer reactions 5

Appendix 139 140 141 142 143 144 145 146 147 148 030608 #479 mAU 500 mat6074-B-RAC-ODH UV_VIS_3 WVL:254 nm 450 400 350 - 11. 573 300 250 200 - 17. 707 150 100 50 - 9. 740 - 12. 933 mi n -50 0.0 2,000 5.0 10.0 030608 #478 [modi fi ed by T CH] mAU 15.0 20.0 27.0 mat6074-B-ODH UV_VIS_3 WVL:254 nm 1,800 - 11. 593 1,600 1,400 1,200 1,000 800 600 400 200 - 18. 100 mi n -200 0.0 No. 5.0 Ret.Time 10.0 Peak Name 15.0 20.0 25.0 Height Area Rel.Area mAU mAU*min % 11.59 n.a. 1681.834 1166.390 95.96 18.10 n.a. 39.173 49.108 4.04 1721.007 1215.498 100.00 Total: ee 92% 204 030608 #531 [modi fi ed by T CH] mAU 300 mat6110-3-ODH UV_VIS_1 WVL:210 nm 275 250 225 200 - 12. 967 175 150 - 14. 587 125 100 75 50 25 mi n -20 0.0 1,800 2.5 5.0 7.5 030608 #532 [modi fi ed by T CH] mAU 10.0 12.5 15.0 17.5 mat6076-A-odh 22.0 UV_VIS_1 WVL:210 nm 1,600 1,400 1,200 1,000 - 12. 900 800 600 400 200 - 15. 113 mi n -100 0.0 No. 2.5 Ret.Time 5.0 7.5 Peak Name 10.0 12.5 15.0 17.5 22.0 Height Area Rel.Area mAU mAU*min % 12.90 n.a. 944.163 671.859 95.29 15.11 n.a. 39.012 33.179 4.71 983.176 705.039 100.00 Total: ee 91% 205 1,000 030608 #535 [modi fi ed by T CH] mAU mat6131-odh UV_VIS_3 WVL:254 nm 900 800 700 600 500 - 6. 013 400 300 200 - 10. 993 100 mi n -50 0.0 1,600 2.0 4.0 6.0 030608 #537 [modi fi ed by T CH] mAU 8.0 10.0 12.0 14.0 mat6176-b-odh 17.0 UV_VIS_3 WVL:254 nm 1,375 1,250 1,125 1,000 - 6. 040 875 750 625 500 375 250 125 - 11. 793 mi n -100 0.0 No. 2.0 Ret.Time 4.0 6.0 Peak Name 8.0 10.0 12.0 14.0 17.0 Height Area Rel.Area mAU mAU*min % 6.04 n.a. 877.802 292.215 93.39 11.79 n.a. 24.652 20.671 6.61 902.454 312.886 100.00 Total: ee 87% 206 1,100 030608 #494 [modi fi ed by T CH] mAU mat6075--rac-ODH UV_VIS_1 WVL:210 nm 1,000 900 - 5. 560 800 700 600 - 6. 960 500 400 300 200 100 mi n -100 0.0 2,000 2.0 4.0 030608 #493 [modi fi ed by T CH] mAU 6.0 8.0 10.0 12.0 mat6075-ODH 14.0 UV_VIS_1 WVL:210 nm 1,800 1,600 - 5. 613 1,400 1,200 1,000 800 600 400 200 - 7. 240 mi n -200 0.0 No. 2.0 Ret.Time 4.0 6.0 Peak Name 8.0 10.0 12.0 14.0 Height Area Rel.Area mAU mAU*min % 5.61 n.a. 1437.653 427.514 95.75 7.24 n.a. 44.017 18.986 4.25 1481.670 446.500 100.00 Total: ee 91% 207 030608 #501 [modi fi ed by T CH] mAU 60.0 mat6077-A-ODH UV_VIS_3 WVL:254 nm 55.0 50.0 45.0 - 6. 120 40.0 - 10. 147 35.0 30.0 25.0 20.0 15.0 10.0 5.0 0.0 mi n -5.0 0.0 1,000 2.0 4.0 6.0 030608 #487 [modi fi ed by T CH] mAU 8.0 10.0 12.0 mat6077-A-ODH 15.0 UV_VIS_3 WVL:254 nm 900 800 700 - 6. 093 600 500 400 300 200 100 - 10. 740 mi n -100 0.0 No. 2.0 Ret.Time 4.0 6.0 Peak Name 8.0 10.0 12.0 15.0 Height Area Rel.Area mAU mAU*min % 6.09 n.a. 598.900 200.838 94.81 10.74 n.a. 21.665 10.998 5.19 620.565 211.836 100.00 Total: ee 90% 208 030608 #482 [modi fi ed by T CH] mAU 500 mat6077-B-RAC-ODH UV_VIS_2 WVL:230 nm 450 400 350 300 250 200 - 13. 360 150 100 - 28. 333 50 mi n -20 0.0 5.0 10.0 15.0 030608 #483 [modi fi ed by T CH] mAU 800 20.0 25.0 30.0 mat6077-B-ODH 35.0 40.0 UV_VIS_2 WVL:230 nm 700 600 - 13. 313 500 400 300 200 100 - 30. 553 mi n -100 0.0 No. 5.0 Ret.Time 10.0 15.0 Peak Name 20.0 25.0 30.0 35.0 Height Area Rel.Area mAU mAU*min % 13.31 n.a. 558.294 417.007 94.85 30.55 n.a. 12.082 22.636 5.15 570.376 439.643 100.00 Total: 40.0 ee 90% 209 030608 #63 [modi fi ed by T CH] mAU 3,500 mat7099-ADH UV_VIS_3 WVL:254 nm 3,000 2,500 2,000 - 9. 473 - 7. 313 1,500 1,000 500 mi n -200 0.0 2.0 4.0 030608 #88 [modi fi ed by T CH] mAU 700 6.0 8.0 10.0 mat7129-A-ADH 12.8 UV_VIS_3 WVL:254 nm 600 500 400 - 7. 260 300 200 100 - 9. 400 mi n -50 0.0 No. 2.0 Ret.Time 4.0 Peak Name 6.0 8.0 10.0 12.8 Height Area Rel.Area mAU mAU*min % 7.26 n.a. 318.883 143.896 93.65 9.40 n.a. 18.818 9.753 6.35 337.701 153.649 100.00 Total: ee 87% 210 2,000 030608 #230 [modi fi ed by T CH] mAU mat9092-ADH UV_VIS_2 WVL:230 nm 1,800 1,600 1,400 1,200 1,000 - 6. 860 - 5. 987 800 600 400 200 -100 4.00 No. mi n 5.00 Ret.Time 6.00 7.00 Peak Name 8.00 9.00 10.00 Height Area Rel.Area mAU mAU*min % 5.99 n.a. 872.846 250.162 50.36 6.86 n.a. 914.309 246.581 49.64 1787.155 496.743 100.00 Total: 700 030608 #229 [modi fi ed by T CH] mAU mat9092--2-ADH UV_VIS_2 WVL:230 nm 600 500 400 - 6. 007 300 200 100 - 6. 887 -50 4.00 No. mi n 5.00 Ret.Time 6.00 Peak Name 7.00 8.00 9.50 Height Area Rel.Area mAU mAU*min % 6.01 n.a. 373.696 100.775 95.96 6.89 n.a. 17.796 4.248 4.04 391.491 105.023 100.00 Total: ee 92% ee 211 1,500 030608 #522 [modi fi ed by T CH] mAU mat6126-2-aDH UV_VIS_3 WVL:254 nm 1,375 1,250 1,125 1,000 - 13. 167 875 - 17. 867 750 625 500 375 250 125 mi n -100 0.0 2,000 2.5 5.0 7.5 030608 #538 [modi fi ed by T CH] mAU 10.0 12.5 15.0 17.5 mat6129-2 22.0 UV_VIS_3 WVL:254 nm 1,800 1,600 1,400 - 17. 920 1,200 1,000 800 600 400 200 - 13. 267 mi n -200 0.0 No. 2.5 Ret.Time 5.0 7.5 Peak Name 10.0 12.5 15.0 17.5 22.0 Height Area Rel.Area mAU mAU*min % 13.27 n.a. 75.460 32.129 4.08 17.92 n.a. 1358.979 754.747 95.92 1434.439 786.876 100.00 Total: ee 92% 212 030608 #525 [modified by TCH] mAU 800 mat6126-3-IA UV_VIS_1 WVL:210 nm 700 600 500 400 - 7.693 - 12.260 300 200 - 6.900 100 - 10.647 -50 0.0 2.0 4.0 6.0 030608 #528 [modified by TCH] mAU 1,800 8.0 10.0 12.0 14.0 mat6069-A-3-IA 17.5 UV_VIS_1 WVL:210 nm 1,600 1,400 - 7.707 1,200 1,000 800 600 400 200 - 12.380 -200 0.0 No. 2.0 4.0 Ret.Time 6.0 Peak Name 8.0 10.0 12.0 14.0 17.5 Height Area Rel.Area mAU mAU*min % 7.71 n.a. 1212.995 436.443 96.27 12.38 n.a. 51.834 16.929 3.73 1264.830 453.373 100.00 Total: ee 92% 213 030608 #444 [modified by TCH] mAU 1,000 mat6064-B-ADH UV_VIS_3 WVL:254 nm 900 800 700 - 5.433 600 500 400 300 - 14.213 200 100 -100 0.0 2.0 4.0 6.0 030608 #492 [modified by TCH] mAU 400 8.0 10.0 12.0 14.0 mat6091-adh 17.5 UV_VIS_3 WVL:254 nm 350 300 250 - 14.633 200 150 100 - 5.507 50 -50 0.0 No. 2.0 4.0 Ret.Time 6.0 8.0 Peak Name 10.0 12.0 14.0 17.5 Height Area Rel.Area mAU mAU*min % 5.51 n.a. 47.208 10.760 7.10 14.63 n.a. 228.291 140.818 92.90 275.499 151.578 100.00 Total: ee 85% 214 030608 #104 [modified by TCH] mAU 400 mat7142-iC UV_VIS_1 WVL:210 nm 350 300 250 200 - 9.360 150 - 15.293 100 50 -20 0.0 5.0 10.0 030608 #110 [modified by TCH] mAU 600 15.0 20.0 mat7145-2-IC 25.0 UV_VIS_1 WVL:210 nm 550 500 450 400 - 15.247 350 300 250 200 150 - 9.500 100 50 -50 0.0 No. 5.0 Ret.Time 10.0 Peak Name 15.0 25.0 20.0 Height Area Rel.Area mAU mAU*min % 9.50 n.a. 46.274 16.116 8.38 15.25 n.a. 263.911 176.131 91.62 310.185 192.247 100.00 Total: ee 83% 215 After re-crystallization 030608 #104 [modi fi ed by T CH] mAU 400 mat7142-i C UV_VIS_1 WVL:210 nm 350 300 250 200 - 9. 360 150 - 15. 293 100 50 mi n -20 0.0 5.0 10.0 030608 #118 [modi fi ed by T CH] mAU 1,000 15.0 20.0 mat7149-IC 25.0 UV_VIS_1 WVL:210 nm 900 800 700 600 - 15. 147 500 400 300 200 100 - 9. 500 mi n -100 0.0 No. 5.0 Ret.Time 10.0 Peak Name 15.0 20.0 25.0 Height Area Rel.Area mAU mAU*min % 9.50 n.a. 19.583 7.451 2.02 15.15 n.a. 509.806 361.283 97.98 529.389 368.734 100.00 Total: ee 96% 216 Ee 73.3% 217 After re-crystallization 030608 #231 [modi fi ed by T CH] mAU 800 mat9085-rac-ODH UV_VIS_2 WVL:230 nm 700 600 500 - 4. 320 400 - 5. 893 300 200 100 mi n -50 0.0 1.3 No. 2.5 Ret.Time 3.8 5.0 Peak Name 6.3 7.5 8.8 10.4 Height Area Rel.Area mAU mAU*min % 4.32 n.a. 471.929 191.909 49.88 5.89 n.a. 337.453 192.835 50.12 809.382 384.744 100.00 Total: 5,000 030608 #232 [modi fi ed by T CH] mAU mat9085-recry-ODH UV_VIS_2 WVL:230 nm 4,500 4,000 3,500 3,000 2,500 - 4. 267 2,000 1,500 1,000 500 - 5. 927 -500 0.00 No. mi n 1.00 Ret.Time 2.00 3.00 Peak Name 4.00 5.00 6.00 7.00 8.00 Height Area Rel.Area mAU mAU*min % 4.27 n.a. 2222.850 1093.437 98.17 5.93 n.a. 40.467 26.496 1.83 2263.317 1119.934 100.00 Total: Ee 96% 218 8.88 Publications 1. Ting Ma, Xiao Fu, Choon Wee Kee, Lili Zong, Yuanhang Pan, Kuo-Wei Huang, and Choon-Hong Tan. Pentanidium Catalyzed Enantioselective Phase-Transfer Conjugate Addition Reactions Journal. American. Chemical. Society., 2011, 133, 2828–2831 2. Yuanhang Pan, Choon Wee Kee, Prof. Zhiyong Jiang, Ting Ma, Yujun Zhao, Yuanyong Yang, Hansong Xue, Prof. Choon-Hong Tan. Expanding the Utility of Brønsted Base Catalysis: Biomimetic Enantioselective Decarboxylative Reactions. Chemistry - A European Journal, 2011, 17, 8363–8370. 3. Zhiyong Jiang, Yuanhang Pan, Yujun Zhao, Ting Ma, Richmond Lee, Yuanyong Yang, Kuo-Wei Huang and Choon Hong Tan. Synthesis of Chiral Quaternary C-F Bond through Highly Enantioselective and Diastereoselective GuanidineCatalyzed Addition of Fluorocarbon Nucleophiles, Angewandte Chemie International Edition, 2009, 48, 3627-3631. 4. Yuanhang Pan, Yujun Zhao, Ting Ma, Yuanyong Yang, Hongjun Liu, Zhiyong Jiang, Choon-Hong Tan, Enantioselective Synthesis of α-Fluorinated β-Amino Acid Derivatives via Asymmetric Mannich Reaction and Selective Decarboxylation/Deacylation Reactions, Chemistry - An European Journal, 2010, 16, 779-782. 5. Xiao Fu, Wei-Tian Loh, Yan Zhang, Tao Chen, Ting Ma, Hongjun Liu, Jianmin Wang, Choon-Hong Tan Prof. Chiral Guanidinium Salt Catalyzed Enantioselective Phospha-Mannich Reactions, Angewandte Chemie International Edition, 2009, 48, 7387–7390, 219 [...]...149 150 151 152 153 154 155 156 157 158 159 160 161 162 163 164 1 65 166 167 168 169 170 171 172 173 174 . 1 45 146 147 148 149 150 151 152 153 154 155 . 152 153 154 155 156 157 158