Table 2.
Substrate scope of amino ester imine additions to methyl acrylate.
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| entry | product | 5 (mol %) | time (h) | 17 yield (%)a | 17 % eeb | 18 yield (%)a |
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| 1 |
17a |
10 | 16 | 73 | 93 | 19 |
| 2 |
17b |
20 | 48 | 70 | 87 | 11 |
| 3 |
17c |
20 | 48 | 67 | 82 | 13 |
| 4 |
17d |
20 | 48 | 54 | 82 | 11 |
| 5 |
17e |
20 | 48 | 46 | 80 | 9 |
| 6 |
17f |
20 | 48 | 62 | 77 | 10 |
| 7 |
17g |
15 | 48 | 77 | 75 | 21 |
| 8 |
17h |
20 | 48 | 0 | – | 0 |
| 9 |
17i |
10 | 48 | 69 | 94 | 23 |
| 10 |
17j |
10 | 16 | 64 | 88 | 20 |
| 11 |
17k |
10 | 16 | 76 | 84 | 19 |
| 12 |
17l |
10 | 16 | 75 | 16 | 16 |
aCalculated based on isolated and purified material. The minor products 18 were isolated as single diastereomers, but the % ee was not determined. bDetermined by HPLC or by 1H NMR using Eu(hfc)3 as a chiral shift reagent.