Table 1. Condition optimization.
entry[a] Sub Sol conv (%)[b] ee (%)[c]
1 (E)-1a DCM >99 91
2 (E)-1a EtOAc >99 92
3 (E)-1a toluene NR /
4 (E)-1a MeOH 75 90
5 (E)-1a THF 21 53
6 (E)-1a dioxane >99 90
7 (E)-1a DME 60 24
8 (E)-1a acetone NR /
9[d] (E)-1a EtOAc 60 92
10 (Z)-1a EtOAc >99 -97
11 (E)-1a-Bz EtOAc 25 31
12 (E)-1a-H EtOAc NR /
13 (E)-1a-δ EtOAc NR /
[a] Conditions: 1a (0.2 mmol), (R)-SKP (0.0021 mmol), [Rh(cod)2]SbF6 (0.002 mmol), H2 (50 atm), DCM (2 mL), rt, 12 h, unless otherwise noted. [b] The conversions were calculated from 1H-NMR spectra. [c] The ee values were determined by HPLC using chiral columns. [d] H2 (30 atm). [a] Conditions: 1a (0.2 mmol), (R)-SKP (0.0021 mmol), [Rh(cod)2]SbF6 (0.002 mmol), H2 (50 atm), DCM (2 mL), rt, 12 h, unless otherwise noted. [b] The conversions were calculated from 1H-NMR spectra. [c] The ee values were determined by HPLC using chiral columns. [d] H2 (30 atm). [a] Conditions: 1a (0.2 mmol), (R)-SKP (0.0021 mmol), [Rh(cod)2]SbF6 (0.002 mmol), H2 (50 atm), DCM (2 mL), rt, 12 h, unless otherwise noted. [b] The conversions were calculated from 1H-NMR spectra. [c] The ee values were determined by HPLC using chiral columns. [d] H2 (30 atm). [a] Conditions: 1a (0.2 mmol), (R)-SKP (0.0021 mmol), [Rh(cod)2]SbF6 (0.002 mmol), H2 (50 atm), DCM (2 mL), rt, 12 h, unless otherwise noted. [b] The conversions were calculated from 1H-NMR spectra. [c] The ee values were determined by HPLC using chiral columns. [d] H2 (30 atm). [a] Conditions: 1a (0.2 mmol), (R)-SKP (0.0021 mmol), [Rh(cod)2]SbF6 (0.002 mmol), H2 (50 atm), DCM (2 mL), rt, 12 h, unless otherwise noted. [b] The conversions were calculated from 1H-NMR spectra. [c] The ee values were determined by HPLC using chiral columns. [d] H2 (30 atm).