Table 2.
Entry | Electrophile | Homoallylic Vinyl Ether | Major Product | Yield (%) | dr (Br) eq:axa | dr (OR) |
---|---|---|---|---|---|---|
1 | 64 | >95:5 | 1:1 | |||
2 | 44 | 74:26 | 1:1 | |||
3 | 71 | 89:11 | 7:3b,c | |||
4 | 61 | 95:5 | – | |||
5 | 65 | 88:12 | 1:1 | |||
6 | 36 | 82:18 | 1:1 | |||
7 | 23 | 80:20 | 1:1 | |||
8 | 90 | 92:8 | 7:3d |
Ratios determined by integration of the crude 1H NMR spectra.
Ratio determined by HPLC analysis of the crude material.
Stereochemistry of the major isomer determined by removal of the chiral auxiliary and formation/analysis of both MPTA ester diastereomers.
Ratio of isolated products.