Table 5.
Diastereoselective synthesis of bridged 1,2,3,4-tetrahydroisoquinoline derivatives using modularly designed organocatalyst.
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25 | R1 | R2 | R3 | Yield [%] | ee [%] | dr |
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a | C6H5 | H | Et | 90 | >99 | 94:6 |
b | 4-F-C6H4 | H | Et | 81 | >99 | 97:3 |
c | 4-Cl-C6H4 | H | Et | 90 | 99 | 92:8 |
d | 4-Br-C6H4 | H | Et | 80 | >99 | 90:10 |
e | 4-NC-C6H4 | H | Et | 77 | 99 | 87:13 |
f | 4-Me-C6H4 | H | Et | 76 | 99 | 97:3 |
g | 4-MeO-C6H4 | H | Et | 79 | 97 | 96:4 |
h | 3-Cl-C6H4 | H | Et | 72 | >99 | 88:12 |
i a | 2-F-C6H4 | H | Et | – | – | – |
j a | 2-Cl-C6H4 | H | Et | – | – | – |
k | C6H5 | F | Et | 73 | >99 | 90:10 |
l | C6H5 | MeO | Et | 74 | 99 | 91:9 |
m | Me | H | Et | 56 | 92 | 86:14 |
n | C6H5 | H | Bn | 75 | 99 | 89:11 |
o | 4-Br-C6H4 | H | Bn | 77 | >99 | 93:7 |
aFormation of a complex mixture was observed.