Table 1.
Entry | metal salt | Yield (%)a | anti:synb | ee (%)c |
---|---|---|---|---|
1 | Sc(OTf)3/Ni(OTf)2/Mg(OTf)2 | Trace | — | — |
2 | Y(OTf)3 | 60 | 2.2:1 | 96/−34 |
3 | La(OTf)3 | 58 | 2.7:1 | 92/63 |
4 | Yb(OTf)3 | 46 | 2.2:1 | 84/13 |
5d | Y(OTf)3 | 73 | 5.2:1 | 97/0 |
6d,e | Y(OTf)3 | 74 | 10:1 | 98/N.D. |
Unless otherwise noted, all reactions were performed with metal salt/ligand (1:1, 2.5 mol%), E-1a (0.20 mmol) in CH2ClCH2Cl (1.0 mL) at 25 °C under N2 atmosphere for 24 h. aIsolated yield of anti-isomer. bDetermined by 1H NMR analysis of crude products. cDetermined by HPLC analysis on a chiral stationary phases. dToluene was used as solvent. eAddition of NEt3 (10 mol%) and for 12 h.