Table 1.
Library of N-tosyltetrahydro-β-carbolinepyrrolines 7{1–7}.
 | ||||||
| entry | R1 | yield of 6a (%) | anti:synb | yield of 7a (%) | purityc | |
| 1 |  |
5{1} | 68 6{1} | NA | 28 7{1} | 98% |
| 2 |  |
5{2} | 74 6{2} | 2.5:1 | 17 syn-7{2} | 98% |
| 3 |  |
5{3} | 81 6{3} | 2.1:1 | 23 syn-7{3} | 98% |
| 4 |  |
5{4} | 73 6{4} | 2.4:1 | 11 anti-7{4} 28 syn-7{4} |
98% 98% |
| 5 |  |
5{5} | 75 6{5} | 2.4:1 | 34 anti-7{5} 17 syn-7{5} |
98% 98% |
| 6 |  |
5{6} | 74 6{6} | 1.3:1 | 35 anti-7{6} 10 syn-7{6} |
98% 98% |
| 7 |  |
5{7} | 54 6{7} | 2.7:1 | 12 anti-7{7} 17 syn-7{7} |
98% 98% |
| 8 |  |
5{8} | 89 6{8} | 2.3:1 | NDd | |
| 9 |  |
5{9} | 78 6{9} | 1.2:1 | NDe | |
| 10 |  |
5{10} | 80 6{10} | 1:1.1 | NDd | |
| 11 |  |
5{11} | 70 6{11} | 1.3:1 | NDe | |
| 12 |  |
5{12} | 80 6{12} | 3.5:1 | NDe | |
| 13 |  |
5{13} | 63 6{13} | 1:1.4 | NDe | |
| 14 |  |
5{14} | 58 6{14} | 2.3:1 | NDd | |
| 15 |  |
5{15} | 80 6{15} | 2.3:1 | NDd | |
| 16 |  |
5{16} | 88 6{16} | 1.4:1 | 8 syn-1{16} | 99% |
aIsolated yields; bdr determined by 1H NMR; cpurity established by LCMS/ELS; dcompound 6 detected; ecompound 6 not detected.