Table 1. Conversion and e.e. of the Alkylation Reaction of 1 with 2 in the Presence of Self-Assembliesa.
| entry | amphiphile (assembly) | medium | conv. (%) | e.e. (%) (S–R) |
|---|---|---|---|---|
| I | TBAH | water/CH2Cl2 | 94 ± 2 | –3 ± 3 |
| IIb | TBAH | water | 17 ± 6 | –6 ± 7 |
| III | CTAB (micelle) | water | 95 ± 2 | 5 ± 3 |
| IV | DOPC (liposome) | water | 62 ± 5 | 97 ± 1 |
Unless otherwise notified, all reactions were carried out in water at room temperature (r.t.) for 24 h. [1] = 1.0 mM, [2] = 12 mM, [amphiphiles] = 10 mM, and [NaOH] = 0.3 M.
TBAH in water does not form any particular assembly. Independent experiments were conducted at least three times to calculate the values of conversion and e.e.