Table 2.
Asymmetric Hydrovinylation of Vinylarenes and a 1,3-Dienea
| no. | product | lig. | convn/yieldb,c | sel.d | ee(%)e/conff |
|---|---|---|---|---|---|
| 1. |  |
L1 | >99/82 | >99 | 95, S |
| L3 | >99/79 | >99 | 95, S | ||
| L10 | >99/77 | >99 | 97, S | ||
| 2. |  |
L1 | >99/97 | 98 | 90, S |
| L3 | >99/98 | 99 | 90, S | ||
| L10 | 97/97 | >99 | 96, S | ||
| 3. |  |
L1 | >99/93 | >99 | 90, S |
| L3 | >99/94 | >99 | 95, S | ||
| L10 | >99/98 | >99 | 99, S | ||
| 4. |  |
L1 | >99/90 | >99 | 80, S |
| L3 | >99/93 | >99 | 86, S | ||
| L10 | >99/92 | >99 | 97, S | ||
| 5. |  |
L1 | >99/91 | >99 | 95, S |
| L3 | >99/96 | >99 | 97, S | ||
| L10 | >99/92 | >99 | 97, S | ||
| 6. |  |
L1 | >99/55 | 57 | 84 |
| L3 | >99/96 | 97 | 77 | ||
| L10 | 61/60 | >99 | 80 | ||
| 7. |  |
1 | >99/95 | >99 | 92, R |
| L3 | >99/97 | >99 | 97, R | ||
| L10 | >99/92 | >99 | 94, R | ||
| 8.g |  |
L1 | >99/68 | 71h | >95, R |
| L3 | >99/71 | 72h | 99, R | ||
| L10 | 79/64 | 79h | 99, R |
a
See eq 1 and Supporting Information for further experimental details.
b
Conversion and selectivities determined by GC analysis.
c
Yields determined by isolated mass after column purification.
d
Selectivity for HV product.
e
Determined by GC, except for 5, which was determined by HPLC.
g
5 mol % of catalyst used.
h
Rest isomerized product from starting material, 1-methyl-3,4-dihydronaphthalene.