Table 5.
Menadione alkylation with amino acids by Naturale’s group.
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|
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| Entry | Amino acid | Product | Protective group | Conversion (%) | Yield (%) |
|
| |||||
| 1 |
|
92a | Boc | 74 | 40 |
| 92b | Troc | 89 | 58 | ||
| 92c | Ac | 98 | 49 | ||
| 92d | TFA | 100 | 42 | ||
| 2 |
|
89a | Boc | 96 | 58 |
| 92e | Troc | 100 | 42 | ||
| 92f | Ac | 57 | 13 | ||
| 92g | TFA | 100 | 51 | ||
| 3 |
|
89b | Boc | 88 | 61 |
| 92h | Troc | 86 | 60 | ||
| 92i | Ac | 75 | 54 | ||
| 92j | TFA | 98 | 53 | ||
| 4 |
|
92k | Boc | 0 | 0 |
| 92l | Troc | 35 | 18 | ||
| 92m | Ac | 29 | 16 | ||
| 92n | TFA | 92 | 27 | ||
| 5 |
|
92o | Boc | 0 | 0 |
| 92p | Troc | 42 | 34 | ||
| 92q | Ac | 24 | 24 | ||
| 92r | TFA | 29 | 29 | ||
| 6 |
|
92s | Boc | 100 | 50 |
| 92t | Troc | 100 | 55 | ||
| 92u | Ac | 93 | 57 | ||
| 92v | TFA | 100 | 39 | ||