Table 3.
Effect of Nitrogen Protecting Group and Ester Substituent on Selectivitya
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---|---|---|---|---|---|
ent | nitrogen PG | ester R | R1 | yield, (SM) %a | ee, %b |
1 | Phthalimide | t-Butyl 5a | Ph 6a | 91 | 88 |
2 | Phthalimide | Methyl 5b | Ph 6b | 35 (35) | 10 |
3 | Phthalimide | Cyclohexyl 5c | Ph 6c | 0 | - |
4 | Phthalimide | Benzyl 5d | Ph 6d | 85 | 20 |
5 | Succinimide | t-Butyl 5e | Ph 6e | 61 | 71 |
6 | Tosyl | t-Butyl 5f | Ph 6f | 86 | 81 |
7 | Tosyl | t-Butyl 5f | 4-BrPh 6g | 23 (67) | 84 |
Isolated yields. Yields in parenthesis are for recovered starting materials.
Chiral HPLC analysis.