Table 1. Effect of Organophosphorus Catalyst on Regioselectivity of Transpositive Allylic Reductiona.
| |||
---|---|---|---|
entry | R3Pb | yieldc | ratioc (4:5) |
1 | none | 80 | 9:91 |
2 | 6 | 78 | 18:82 |
3 | 7 | 85 | 11:89 |
4 | 8 | 95 | 19:81 |
5 | 9 | 95 | 54:46 |
6 | 10 | 96 | 94:6 |
7 | 10 d | 100 | 98:2 |
8 | 10 e | 81 | 88:12 |
9 | 11 | 96 | 91:9 |
See Supporting Information for full experimental details.
See ref 17.
The combined yield and ratio of 4 and 5 were determined by GC analysis (dodecane internal standard).
Neutral trivalent 10 as catalyst.
10·HBF4 salt as precatalyst.