Table 1.
Synthesis of a tetrahydronaphthyl amide library
| entry | acid chloride | yield (%)a | drb | major product | purity (%)c | minor product | purity (%)c |
|---|---|---|---|---|---|---|---|
| 1 | 10 (R = C(H)Me2) | 52 | 3:1 | 23{1} | 100 | 24{1} | 100 |
| 2 | 12 (R = CH=CHMe) | 59 | 3:1 | 23{2} | 92 | 24{2} | 99 |
| 3 | 13 (R = CH2OMe) | 34 | 3:1 | 23{3} | 100 | 24{3} | 99 |
| 4 | 14 (R = CH2OPh) | 73 | 3:1 | 23{4} | 100 | 24{4} | 100 |
| 5 | 15 (R = CH2OBn) | 39 | 4:1 | 23{5} | 100 | 24{5} | 99 |
| 6 | 16 (R = CH2PhOMe) | 41 | 3:1 | 23{6} | 100 | 24{6} | 99 |
| 7 | 17 (R = CH2Ph) | 34 | 3:1 | 23{7} | 100 | 24{7} | 98 |
| 8 | 18 (R = CH2PhF) | 50 | 3:1 | 23{8} | 100 | 24{8} | 98 |
| 9 | 19 (R = CH2C4H3S) | 51 | 9:1 | 23{9} | 100 | 24{9} | 100 |
| 10 | 20 (R = CH2CH2Ph) | 54 | 3:1 | 23{10} | 100 | 24{10} | 100 |
| 11 | 21 (R = Ph-Ph) | 16 | 4:1 | 23{11} | 100 | 24{11} | 93 |
| 12 | 22 (R = PhCF3) | 28 | 3:1 | 23{12} | 100 | 24{12} | 100 |
a
Isolated yield.
b
dr = ratio of the diastereomers.
c
UV purities determined at 214 nm after preparative HPLC.