Table 2.

Scope of aldehydes and Grignard reagents in 1,2-diol synthesis.^[a–^f]

^[a]R=Prⁱ (2a–k), Ph (2l–r), allyl (2s–v).

^[b]10 mol% 1 or L-proline used.

^[c]5 equiv Grignard reagent and 5 equiv CeCl₃·2LiCl used.

^[d]Absolute configuration determined by comparison of specific rotation.

^[e]dr determined by ¹H NMR. Ratios in parentheses determined by GC.

^[f]Isolated yield of two diastereomers. Based on nitrosotoluene.

^[g]R’Li used instead of R’MgCl.

^[h]Arylmagnesium bromide used.

^[i]Grignard reagent reacted with CeCl₃·2LiCl at RT.

^[j]The addition reaction warmed to 0°C.