Table 3.

TRIP‐catalyzed allylation of different ketones under optimized conditions.

Reaction conditions: Ketone (0.1 mmol), zinc (5 eq.), NH₄Cl (8 eq.), (S)‐TRIP [(S)‐9, 10 mol‐%], 7 d (1.5 eq.), 0.5–2 mL toluene/cyclohexane mixture (for details see ESI); stirred at rt for 16 h.

^[a] Isolated yields are given.

^[b] The enantiomeric excess was determined on a chiral stationary phase via normal phase HPLC‐UV.

^[c] (R)‐TRIP [(R)‐9, 10 mol‐%] was used.

^[d] Benzhydryl (Z)‐2‐(bromomethyl)but‐2‐enoate (7 e) was used as allylating reagent.

^[e] The diastereomeric ratio (d.r.) was determined via ¹H‐NMR (given in brackets); relative stereoconfiguration was determined by ¹H,¹H‐NOESY spectra of lactone 10 q (see Scheme 3 and the ESI).